No renderable structure data available
C1=C2C(=CC(=C1S(=O)(=O)N)Cl)C(=O)NC2=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 6-chloro-1,3-dioxoisoindole-5-sulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 3861-99-2 |
| Database ID | 19733 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
6-chloro-1,3-dioxoisoindole-5-sulfonamide (CAS 3861-99-2) 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 19733
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-27df00bd97d84e99befe9fff15956657Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d8ffe4cf43bc4a098589bcaed3e59e56Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (10.1 g., 0.0386 mole) and 4-amino-1-(3-trifluoromethylbenzyl)piperidine (10.0 g., 0.0386 mole) in 200 ml. of n-pentanol according to the procedure of Example 1(a) afforded the crude 1,3-dioxoisoindole product purified by chromatography to yield 8.1 g. (42% yield) of 6-chloro-2,3-dihydro-1,3-dioxo-2-[1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide. The NMR spectral data was consistent for the compound used without further purification below.
Source ID: ord-e74e18e5ef02406a8c173ea654bdb8efConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (4.54 g., 0.0174 mole) and 4-amino-1-[4-(2-propenyloxy)benzyl]piperidine (4.29 g., 0.0174 mole) in 100 ml. of n-pentanol at reflux temperature for 24 hrs. according to the procedure of Example 1(a) afforded crude 1,3-dioxoisoindole product. Purification was carried out by treating with methanol-decolorizing charcoal followed by trituration with ether to afford 4.8 g. (57%) of the 1,3-dioxoisoindole used without further purification below.
Source ID: ord-93f67a613d834704a939bf4a90a003e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (4.54 g., 0.0174 mole) and 4-amino-1-[4-(2-propenyloxy)benzyl]piperidine (4.29 g., 0.0174 mole) in 100 ml. of n-pentanol at reflux temperature for 24 hrs. according to the procedure of Example 1(a) afforded crude 1,3-dioxoisoindole product. Purification was carried out by treating with methanol-decolorizing charcoal followed by trituration with ether to afford 4.8 g. (57%) of the 1,3-dioxoisoindole used without further purification below.
Source ID: ord-93f67a613d834704a939bf4a90a003e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-chloro-5-sulfamoylphthalimide (21.3 g., 0.076 mole) and 250 ml. of liquid ammonia was stirred at room temperature while permitting ammonia to evaporate. Water was added to residual material, the pH adjusted to 7 with hydrochloric acid and precipitated material collected to provide 14.5 g. (63%) of hydrated 4-chloro-5-(sulfamoyl)-1,2-benzenedicarboxamide, m.p. 270°-275° C. to evaporate Water was added to residual material precipitated material collected to provide 14.5 g
Source ID: ord-01621d922c4a45f2b8e94e088ed30e71Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (5.21 g., 0.02 mole) and 4-amino-1-(4-methoxybenzyl)piperidine (4.5 g., 0.02 mole) in 80 ml. of n-pentanol according to the procedure of Example 1(a) afforded the crude 1,3-dioxoisoindole product purified by chromatography (silica gel, ethyl acetate-n-hexane) to yield 2.88 g. (31%) of 6-chloro-2,3-dihydro-2-[1-[(4-methoxyphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide. The NMR spectral data was consistent for the compound used without further purification below.
Source ID: ord-811d287b556843758a248cc3e7519b32Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (5.21 g., 0.02 mole) and 4-amino-1-(4-methoxybenzyl)piperidine (4.5 g., 0.02 mole) in 80 ml. of n-pentanol according to the procedure of Example 1(a) afforded the crude 1,3-dioxoisoindole product purified by chromatography (silica gel, ethyl acetate-n-hexane) to yield 2.88 g. (31%) of 6-chloro-2,3-dihydro-2-[1-[(4-methoxyphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide. The NMR spectral data was consistent for the compound used without further purification below.
Source ID: ord-811d287b556843758a248cc3e7519b32Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-chloro-5-sulfamoylphthalimide (5.74 g., 0.022 mole) and 4-amino-1-[(2-methylphenyl)methyl]piperidine (4.5 g., 0.022 mole) in 85 ml. of n-pentanol was reacted according to the procedure of Example 1(a). Addition of n-heptane to the reaction mixture afforded 7.9 g. (80%) of the 1,3-dioxoisoindole product, m.p. 283°-243°. Crystallization of this material from DMF-methanol provided analytically pure 6-chloro-2,3-dihydro-2-[1-[(2-methylphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 244°-245° (dec.). afforded 7.9 g Crystallization of this material from DMF-methanol
Source ID: ord-aa54ee27ac754616ae29fd99a2216abcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of a mixture of 4-chloro-5-sulfamoylphthalimide (6.48 g., 0.025 mole) and 4-amino-1-(4-bromobenzyl)piperidine (6.7 g., 0.025 mole) in n-pentanol according to the procedure of Example 1(a) afforded the 1,3-dioxoisoindole product. Purification of the crude product by triturating with n-heptane and crystallization from DMF-methanol afforded 6.9 g. (54%) of 2-[1-[(4-bromophenyl)methyl]-4-piperidinyl]-6-chloro-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 246°-247° (dec.).
Source ID: ord-4e3d973ab3094fd1b69a9e76759707aaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of a mixture of 4-chloro-5-sulfamoylphthalimide (6.48 g., 0.025 mole) and 4-amino-1-(4-bromobenzyl)piperidine (6.7 g., 0.025 mole) in n-pentanol according to the procedure of Example 1(a) afforded the 1,3-dioxoisoindole product. Purification of the crude product by triturating with n-heptane and crystallization from DMF-methanol afforded 6.9 g. (54%) of 2-[1-[(4-bromophenyl)methyl]-4-piperidinyl]-6-chloro-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 246°-247° (dec.).
Source ID: ord-4e3d973ab3094fd1b69a9e76759707aaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of 4-chloro-5-sulfamoylphthalimide (5.57 g., 0.0214 mole) and 4-amino-1-(4-chlorobenzyl)piperidine (4.8 g., 0.0214 mole) in 85 ml. of n-pentanol according to the procedure of Example 1(a) with heating at 130°-138° for a 48 hr. period afforded 7.07 g. (71%) m.p. 248°-250° (dec.) of the 1,3-dioxoisoindole product. A sample crystallized from dimethylformamide-methanol provided analytically pure 6-chloro-2-[1-[(4-chlorophenyl)methyl]-4-piperidinyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 250°-251° (dec.). period afforded 7.07 g A sample crystallized from dimethylformamide-methanol
Source ID: ord-691cd2b016f94d458983ed72bf182b8cPubChem References
These sources are listed in the compound's public database record.
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