No renderable structure data available
COC(=O)COC1=CC=C(C=C1)CC2C(=O)NC(=O)S2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 185428-88-0 |
| Database ID | 23514198 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate (CAS 185428-88-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 23514198
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-412cb035a187489ba1db9557b3d3bf03Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5-methoxy-N-methyl-1,2-phenylenediamine (21.8 g), 5-(4-methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione (63.4 g), 1,4-dioxane (250 mg) and concentrated hydrochloric acid (750 ml) was heated under reflux for 60 hours. The reaction mixture was cooled in an ice bath and the precipitated crystals were filtered. To the crystals were added 5% aqueous sodium hydrogencarbonate solution (800 ml) and the mixture was stirred at room temperature for 2 hours. The mixture was filtered and the insoluble material was collected by filtration and dissolved in a mixture of N,N-dimethylformamide (1000 ml) and methanol (200 ml) and decolorized with active charcoal. The active charcoal was removed by filtration and the filtrate was concentrated to about 50 ml. To the solution was added diethyl ether (750 ml) and allowed to stand at room temperature for 2 days. The precipitated crystals were filtered to give the desired product (20.1 g, yield 35%, melting point 267-271° C., Rf=0.68: chromatography on a silica gel thin layer using 5% ethanol-methylene chloride as the eluant). was heated under reflux for 60 hours The reaction mixture was cooled in an ice bath the precipitated crystals were filtered To the crystals were added 5% aqueous sodium hydrogencarbonate solution (800 ml) The mixture was filtered the insoluble material was collected by filtration dissolved in a mixture of N,N-dimethylformamide (1000 ml) and methanol (200 ml) The active charcoal was removed by filtration the filtrate was concentrated to about 50 ml To the solution was added diethyl ether (750 ml) to stand at room temperature for 2 days The precipitated crystals were filtered
Source ID: ord-7276feb779a84eb4ac7814f89f44ad12Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5-methoxy-N-methyl-1,2-phenylenediamine (21.8 g), 5-(4-methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione (63.4 g), 1,4-dioxane (250 mg) and concentrated hydrochloric acid (750 ml) was heated under reflux for 60 hours. The reaction mixture was cooled in an ice bath and the precipitated crystals were filtered. To the crystals were added 5% aqueous sodium hydrogencarbonate solution (800 ml) and the mixture was stirred at room temperature for 2 hours. The mixture was filtered and the insoluble material was collected by filtration and dissolved in a mixture of N,N-dimethylformamide (1000 ml) and methanol (200 ml) and decolorized with active charcoal. The active charcoal was removed by filtration and the filtrate was concentrated to about 50 ml. To the solution was added diethyl ether (750 ml) and allowed to stand at room temperature for 2 days. The precipitated crystals were filtered to give the desired product (20.1 g, yield 35%, melting point 267-271° C., Rf=0.68: chromatography on a silica gel thin layer using 5% ethanol-methylene chloride as the eluant). was heated under reflux for 60 hours The reaction mixture was cooled in an ice bath the precipitated crystals were filtered To the crystals were added 5% aqueous sodium hydrogencarbonate solution (800 ml) The mixture was filtered the insoluble material was collected by filtration dissolved in a mixture of N,N-dimethylformamide (1000 ml) and methanol (200 ml) The active charcoal was removed by filtration the filtrate was concentrated to about 50 ml To the solution was added diethyl ether (750 ml) to stand at room temperature for 2 days The precipitated crystals were filtered
Source ID: ord-7276feb779a84eb4ac7814f89f44ad12Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in Examples 23 or 24 (100 g, 0.34 M), N-methyl anthranilamide (58.7 g, 0.39 M), xylene (100 ml) and p-toluenesulfonic acid (200 mg) was taken in a round bottom flask fitted with a mechanical stirrer, oil bath and Dean-Stark condenser. The reaction mixture was heated to reflux (internal temperature 150-155° C., oil bath temperature 170-180° C.) for a period of 10-15 h while monitoring the reaction by TLC. After completion of the reaction, reaction mass was cooled to 80° C. and methanol (700 ml) was added slowly through a dropping funnel. The reaction mass was allowed to attain room temperature while stirring and the solid thus obtained was filtered and washed with methanol (150 ml) and dried at 100-120° C. for 1 h to afford 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione as a white solid (30 g, Y=23%, P=98%). obtained was taken in a round bottom flask fitted with a mechanical stirrer, oil bath The reaction mixture was heated the reaction by TLC After completion of the reaction, reaction mass was cooled to 80° C. to attain room temperature the solid thus obtained was filtered washed with methanol (150 ml) dried at 100-120° C. for 1 h
Source ID: ord-bf6c21fe207b47fd80eff12d03af14a1Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in Examples 23 or 24 (100 g, 0.34 M), N-methyl anthranilamide (58.7 g, 0.39 M) and p-toluenesulfonic acid (˜200 mg) was taken in a round bottom flask fitted with a mechanical stirrer, oil bath and Dean-Stark condenser. The reaction mixture was heated to reflux (Internal temperature 150-155° C. oil bath temperature 170-180° C.) for a period of 10-15 h while monitoring the reaction by TLC. After completion of the reaction, reaction mass was cooled to 80° C. and methanol (700 ml) was added slowly through a dropping funnel. The reaction mass was allowed to attain room temperature while stirring and the solid thus obtained was filtered and washed with methanol (150 ml) and dried at 100-120° C. for 1 h to afford 5-[4-[[-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione as a white solid (28 g, Y=23%, P=98%). obtained was taken in a round bottom flask fitted with a mechanical stirrer, oil bath The reaction mixture was heated the reaction by TLC After completion of the reaction, reaction mass was cooled to 80° C. to attain room temperature the solid thus obtained was filtered washed with methanol (150 ml) dried at 100-120° C. for 1 h
Source ID: ord-e99116cd36dc4762a1e921f0551f1080Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in Example 23 or 24 (100 g, 0.34 M), N-methyl anthranilamide (58.7 g, 0.39 M), xylene (100 ml) and p-toluenesulfonic acid (˜200 mg) was taken in a round bottom flask fitted with a mechanical stirrer, oil bath and Dean-Stark condenser. The reaction mixture was heated to reflux (Internal temperature 150-155° C., oil bath temperature 170-180° C.) for a period of 45-55 h while monitoring the reaction by TLC. After completion of the reaction, the reaction mass was cooled to 80° C. and methanol (700 ml) was added slowly through a dropping funnel. The reaction mass was allowed to attain room temperature while stirring and the solid thus obtained was filtered and washed with methanol (150 ml) and dried at 100-120° C. for 1 h to afford 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione as a white solid (66 g, Y=49%, P=98%). obtained was taken in a round bottom flask fitted with a mechanical stirrer, oil bath The reaction mixture was heated the reaction by TLC After completion of the reaction the reaction mass was cooled to 80° C. to attain room temperature the solid thus obtained was filtered washed with methanol (150 ml) dried at 100-120° C. for 1 h
Source ID: ord-c751708f5f4f4148abd68d79f57eb036Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione (100 g, 0.34 M) obtained in Example 23 or 24, N-methyl anthranilamide (58.7 g, 0.39 M) and p-toluenesulfonic acid (200 mg) was taken in a round bottom flask fitted with a mechanical stirrer, oil bath and Dean-Stark condenser. The reaction mixture was heated to reflux (Internal temperature 150-155° C., oil bath temperature 170-180° C.) for a period of 45-55 h while monitoring the reaction by TLC. After completion of the reaction, the reaction mass was cooled to 80° C. and methanol (700 ml) was added slowly through a dropping funnel. The reaction mass was allowed to attain room temperature while stirring and the solid thus obtained was filtered and washed with methanol (150 ml) and dried at 100-120° C. for 1 h to afford 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione as a white solid (71 g, Y=53%, P=98%). was taken in a round bottom flask fitted with a mechanical stirrer, oil bath The reaction mixture was heated the reaction by TLC After completion of the reaction the reaction mass was cooled to 80° C. to attain room temperature the solid thus obtained was filtered washed with methanol (150 ml) dried at 100-120° C. for 1 h
Source ID: ord-29de6bcd1d2d471ea2d8cf093b26b2b3Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione (100 g, 0.34 M) obtained in Example 23 or 24, N-methyl anthranilamide (58.7 g, 0.39 M) and p-toluenesulfonic acid (200 mg) was taken in a round bottom flask fitted with a mechanical stirrer, oil bath and Dean-Stark condenser. The reaction mixture was heated to reflux (Internal temperature 150-155° C., oil bath temperature 170-180° C.) for a period of 45-55 h while monitoring the reaction by TLC. After completion of the reaction, the reaction mass was cooled to 80° C. and methanol (700 ml) was added slowly through a dropping funnel. The reaction mass was allowed to attain room temperature while stirring and the solid thus obtained was filtered and washed with methanol (150 ml) and dried at 100-120° C. for 1 h to afford 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione as a white solid (71 g, Y=53%, P=98%). was taken in a round bottom flask fitted with a mechanical stirrer, oil bath The reaction mixture was heated the reaction by TLC After completion of the reaction the reaction mass was cooled to 80° C. to attain room temperature the solid thus obtained was filtered washed with methanol (150 ml) dried at 100-120° C. for 1 h
Source ID: ord-29de6bcd1d2d471ea2d8cf093b26b2b3Conditions: temp:12.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in any of Examples 23-24 (135 g, 0.46 M) and water (540 ml, 4 times w/v) was taken in a round bottom flask fitted with a mechanical stirrer. Aq. sodium hydroxide solution (37 g of NaOH in 135 ml of water) was added slowly over a period of 5-10 minutes at 20-25° C. Stirring was continued at ambient temperature for a period of 2-3 h, while monitoring the reaction by TLC. After the completion of the reaction, the pH of the reaction mixture was adjusted to 2 using conc. HCl (temp. raises to 40-45° C.) and allowed to attain room temperature. The mass was cooled to 10-15° C. and the solid thus obtained was filtered and dried at 60-70° C. under 1-2 mm Hg of vacuum to afford 5-[4-[(carboxy)methoxy]benzyl]thiazolidine-2,4-dione (121 g, Y=99%, P=99.2%). obtained was taken in a round bottom flask fitted with a mechanical stirrer the reaction by TLC After the completion of the reaction to attain room temperature the solid thus obtained was filtered dried at 60-70° C. under 1-2 mm Hg of vacuum
Source ID: ord-9af0e96f67c943bca3699cfc16fcfc1eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.8 g of 5-methoxy-N-methyl-1,2-phenylenediamine [prepared as described in step (e) above], 63.4 g of 5-(4-methoxycarbonylmethoxybenzyl)-thiazolidin-2,4-dione [prepared as described in step (g) above], 250 ml of 1,4-dioxane and 750 ml of concentrated aqueous hydrochloric acid was heated under reflux for 60 hours. At the end of this time, the reaction mixture was cooled with ice, after which the solid matter was collected by filtration. 800 ml of a 5% w/v aqueous solution-of sodum hydrogencarbonate was added to this matter, and the resulting mixture was stirred at room temperature for 2 hours. Insoluble materials were then collected by filtration and dissolved in a mixture of 1000 ml of dimethylformamide and 200 ml of methanol. The resulting solution was decolorized by treatment with activated charcoal, which was then removed by filtration. The filtrate was then concentrated by evaporation under reduced pressure to a volume of about 50 ml. The resulting concentrate was added to 750 ml of diethyl ether and the solution thus obtained was allowed to stand for 2 days. At the end of this time, the resulting precipitate was collected by filtration, to give 20.1 g of the title compound, melting at 267°-271° C. and having an Rf value=0.68 (on thin layer chromatography on silica gel; using a developing solvent of methylene chloride containing 5% v/v ethanol). was heated under reflux for 60 hours At the end of this time, the reaction mixture was cooled with ice after which the solid matter was collected by filtration 800 ml of a 5% w/v aqueous solution-of sodum hydrogencarbonate was added to this matter Insoluble materials were then collected by filtration dissolved in a mixture of 1000 ml of dimethylformamide and 200 ml of methanol was then removed by filtration The filtrate was then concentrated by evaporation under reduced pressure to a volume of about 50 ml The resulting concentrate was added to 750 ml of diethyl ether the solution thus obtained to stand for 2 days At the end of this time, the resulting precipitate was collected by filtration
Source ID: ord-1f6f10af141e427db7c837ca3080d359Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1700 ml of acetic acid and then 400 ml of water were added at room temperature to a suspension of 344 g of 5-(4-methoxycarbonylmethoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione [prepared as described in step (f) above] in 400 ml of 1,4-dioxane and the resulting mixture was stirred for 5 hours at 80° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane, a 2 1 by volume mixture of ethyl acetate and hexane and then ethyl acetate as eluents, to give 161.7 g of the title compound, melting at 100°-106° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane a 2 1 by volume mixture of ethyl acetate and hexane
Source ID: ord-289cd1e97bde4fcf80154f258749095bConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1700 ml of acetic acid and then 400 ml of water were added at room temperature to a suspension of 344 g of 5-(4-methoxycarbonylmethoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione [prepared as described in step (f) above] in 400 ml of 1,4-dioxane and the resulting mixture was stirred for 5 hours at 80° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane, a 2 1 by volume mixture of ethyl acetate and hexane and then ethyl acetate as eluents, to give 161.7 g of the title compound, melting at 100°-106° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane a 2 1 by volume mixture of ethyl acetate and hexane
Source ID: ord-289cd1e97bde4fcf80154f258749095bPubChem References
These sources are listed in the compound's public database record.
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