No renderable structure data available
C1=CC(=CC=C1C(=O)NN)IChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-iodobenzohydrazide |
|---|---|
| IUPAC Name | — |
| CAS Number | 39115-95-2 |
| Database ID | 306104 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-iodobenzohydrazide (CAS 39115-95-2) 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 306104
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-aa95e6d971464c31b08344d84af7e7e6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a7ec74c159f140309c774a81c5098046Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 4-iodobenzohydrazide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 430 mg of the title compound (83%) as a yellow solid in 98.7% purity by HPLC (Rt: 6.19, gradient of 10 min, MaxPlot detection between 230 and 400 nm). the reaction mixture was cooled to rt a yellow solid precipitated out Filtration on a fritté washing with AcOH, water drying under vacuo at 60° C. overnight
Source ID: ord-dbbcaed8a50b4f8a9b7bb118e907f6ffConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 4-iodobenzohydrazide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 430 mg of the title compound (83%) as a yellow solid in 98.7% purity by HPLC (Rt: 6.19, gradient of 10 min, MaxPlot detection between 230 and 400 nm). the reaction mixture was cooled to rt a yellow solid precipitated out Filtration on a fritté washing with AcOH, water drying under vacuo at 60° C. overnight
Source ID: ord-dbbcaed8a50b4f8a9b7bb118e907f6ffConditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (5.0 g, 18.6 mmol), 4-iodobenzhydrazide (CAS 39115-95-2, 4.88 g, 18.6 mmol) and 1-hydroxybenzotriazole hydrate (2.85 g, 18.6 mmol) were placed in a 250 mL round bottomed flask. Anhydrous THF (120 mL) was added and the mixture was cooled to −20° C. N-(3-Dimethylaminopropyl)-N′-ethylcarbodimide HCl (5.35 g, 27.9 mmol) was added, followed by Et3N (3.9 mL, 28.0 mmol). The reaction mixture was stirred at −20° C. for 1 h and room temperature for overnight. The reaction was quenched by adding water and extracted with EtOAc, which was washed with 5% aqueous NaOH, water, brine and dried over Na2SO4. The extracts were filtered and the filtrate was concentrated to provide a brown solid, which was purified by flash chromatography (80% EtOAc in hexanes) to afford the title compound (7.3 g, 77%), which was used directly in the next step. The reaction was quenched by adding water extracted with EtOAc, which was washed with 5% aqueous NaOH, water, brine dried over Na2SO4 The extracts were filtered the filtrate was concentrated to provide a brown solid, which was purified by flash chromatography (80% EtOAc in hexanes)
Source ID: ord-7e5a99bc82e84db39fc2fac5d2e0e620Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (5.0 g, 18.6 mmol), 4-iodobenzhydrazide (CAS 3915-95-2, 4.88 g, 18.6 mmol) and 1-hydroxybenzotriazole hydrate (2.85 g, 18.6 mmol) were placed in a 250 mL round bottomed flask. Anhydrous THF (120 mL) was added and the mixture was cooled to −20° C. N-(3-Dimethylaminopropyl)-N′-ethylcarbodimide HCl (5.35 g, 27.9 mmol) was added, followed by Et3N (3.9 mL, 28.0 mmol). The reaction mixture was stirred at −20° C. for h and room temperature for overnight. The reaction was quenched by adding water and extracted with EtOAc, which was washed with 5% aqueous NaOH, water, brine and dried over Na2SO4. The extracts were filtered and the filtrate was concentrated to provide a brown solid, which was purified by flash chromatography (80% EtOAc in hexanes) to afford the title compound (7.3 g, 77%), which was used directly in the next step. The reaction was quenched by adding water extracted with EtOAc, which was washed with 5% aqueous NaOH, water, brine dried over Na2SO4 The extracts were filtered the filtrate was concentrated to provide a brown solid, which was purified by flash chromatography (80% EtOAc in hexanes)
Source ID: ord-f843bfa633d24e168d2d2a02bf395502Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Triethyl orthoacetate (10 ml) was added to 4-iodo-benzoic acid hydrazide (Intermediate 14) (0.55 g, 2.1 mmol) and heated under nitrogen at 130° C. for 3 hours. The triethyl orthoacetate was removed in vacuo and the residue partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate filtered and the solvent removed in vacuo. The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v:v to 5:1 cyclohexane/ethyl acetate v:v. The desired product was obtained as a white solid (0.31 g, 1.1 mmol). The triethyl orthoacetate was removed in vacuo the residue partitioned between ethyl acetate (30 ml) and water (30 ml) The organic layer was washed with water (50 ml), brine (50 ml) dried over magnesium sulfate filtered the solvent removed in vacuo The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v
Source ID: ord-83ed388e738c4ac3a3d041d293b05383Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Trifluoroacetic acid (10 ml) was added to 4iodo-benzoic acid N′-(2,2-dimethyl-propionyl)-hydrazide (Intermediate 13) (1 g, 2.76 mmol) and stirred at room temperature for 2 hours. The trifluoroactic acid was removed in vacuo and the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The desired product was obtained as a white solid (0.55 g, 2.1 mmol). The trifluoroactic acid was removed in vacuo the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml) The organic layer was washed with water (50 ml), brine (50 ml) dried over magnesium sulfate filtered the solvent removed in vacuo
Source ID: ord-ac02ab09da504815b72b4796a3df3564Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-aa95e6d971464c31b08344d84af7e7e6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a7ec74c159f140309c774a81c5098046Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Triethyl orthoacetate (10 ml) was added to 4-iodo-benzoic acid hydrazide (Intermediate 14) (0.55 g, 2.1 mmol) and heated under nitrogen at 130° C. for 3 hours. The triethyl orthoacetate was removed in vacuo and the residue partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate filtered and the solvent removed in vacuo. The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v:v to 5:1 cyclohexane/ethyl acetate v:v. The desired product was obtained as a white solid (0.31 g, 1.1 mmol). The triethyl orthoacetate was removed in vacuo the residue partitioned between ethyl acetate (30 ml) and water (30 ml) The organic layer was washed with water (50 ml), brine (50 ml) dried over magnesium sulfate filtered the solvent removed in vacuo The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v
Source ID: ord-83ed388e738c4ac3a3d041d293b05383Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Trifluoroacetic acid (10 ml) was added to 4iodo-benzoic acid N′-(2,2-dimethyl-propionyl)-hydrazide (Intermediate 13) (1 g, 2.76 mmol) and stirred at room temperature for 2 hours. The trifluoroactic acid was removed in vacuo and the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The desired product was obtained as a white solid (0.55 g, 2.1 mmol). The trifluoroactic acid was removed in vacuo the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml) The organic layer was washed with water (50 ml), brine (50 ml) dried over magnesium sulfate filtered the solvent removed in vacuo
Source ID: ord-ac02ab09da504815b72b4796a3df3564PubChem References
These sources are listed in the compound's public database record.
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