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CN(C)S(=O)(=O)C1=CC=C(C=C1)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-amino-N,N-dimethylbenzenesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 1709-59-7 |
| Database ID | 74369 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-amino-N,N-dimethylbenzenesulfonamide (CAS 1709-59-7) 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 74369
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-3f4664500e414b558e6294a874fd11eaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d5948e9ccfab42d2995053505a92a1bdConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-amino-N,N-dimethylbenzenesulfonamide (3.0 g, 14.98 mmol) in EtOH (165 mL) at 50° C. was added a slurry of iodine (1.3 g, 4.99 mmol) and silver sulfate (2.8 g, 9.00 mmol) in EtOH (40 mL). The same addition was repeated after 1 h of stirring at 50° C., then the reaction mixture was stirred at 50° C. for 16 h. Iodine (0.76 g, 3.00 mmol) was again added, and the mixture stirred at 50° C. for 2 h before being filtered through Celite®. The filtrate was concentrated in vacuo, and EtOH (70 mL) was added. The suspension was stirred at 50° C. for 1 h, cooled to r.t., then filtered to give the title compound (2.7 g, 55%) as a brown solid that was used without further purification. δH (DMSO-d6) 7.81 (1H, d, J 2.1 Hz), 7.42 (1H, dd, J 8.6 and 2.1 Hz), 6.83 (1H, d, J 8.6 Hz), 6.12 (2H, br. s), 2.58 (6H, s). LCMS (ES+) 326.9 (M+H)+, RT 2.50 minutes (Method 3). The same addition the reaction mixture was stirred at 50° C. for 16 h the mixture stirred at 50° C. for 2 h before being filtered through Celite® The filtrate was concentrated in vacuo, and EtOH (70 mL) was added The suspension was stirred at 50° C. for 1 h cooled to r.t. filtered
Source ID: ord-8c6efc0a8e54436eaf6468697e075feaConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-amino-N,N-dimethylbenzenesulfonamide (3.0 g, 14.98 mmol) in EtOH (165 mL) at 50° C. was added a slurry of iodine (1.3 g, 4.99 mmol) and silver sulfate (2.8 g, 9.00 mmol) in EtOH (40 mL). The same addition was repeated after 1 h of stirring at 50° C., then the reaction mixture was stirred at 50° C. for 16 h. Iodine (0.76 g, 3.00 mmol) was again added, and the mixture stirred at 50° C. for 2 h before being filtered through Celite®. The filtrate was concentrated in vacuo, and EtOH (70 mL) was added. The suspension was stirred at 50° C. for 1 h, cooled to r.t., then filtered to give the title compound (2.7 g, 55%) as a brown solid that was used without further purification. δH (DMSO-d6) 7.81 (1H, d, J 2.1 Hz), 7.42 (1H, dd, J 8.6 and 2.1 Hz), 6.83 (1H, d, J 8.6 Hz), 6.12 (2H, br. s), 2.58 (6H, s). LCMS (ES+) 326.9 (M+H)+, RT 2.50 minutes (Method 3). The same addition the reaction mixture was stirred at 50° C. for 16 h the mixture stirred at 50° C. for 2 h before being filtered through Celite® The filtrate was concentrated in vacuo, and EtOH (70 mL) was added The suspension was stirred at 50° C. for 1 h cooled to r.t. filtered
Source ID: ord-8c6efc0a8e54436eaf6468697e075feaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 4-oxazol-5-yl-aniline according to Procedure D: 1H NMR (DMSO-d6): δ10.7 (s, 1H), 8.3 (s, 1H), 7.5 (s, 3H), 6.9 (d, 1H), 4.5 (s, 1H), 2.0 (s, 3H); APCI−M m/z 247 (M+H)+. 5-Oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 3-methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure D: 1H NMR (DMSO-d6): δ10.5 (s, 1H), 8.3 (s, 1H), 7.5 (m, 3H), 6,8 (d, 1H), 3.5 (s, 2H); APCI−MS m/z 201 (M+H)+. 3-Ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure I: 1H NMR (DMSO-d6): δ10.43 (s, 1H), 8.37 (s, 1H), 7.76 (s, 1H), 7.51 (m, 2H), 6.90, (d, 1H), 4.43 (q, 2H), 1.4 (t, 3H): APCI−MS m/z 255 (M−H)+. The title compound was prepared in 36% yield from 3-ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one and N,N-dimethyl-4-aminobenzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ10.9 (d, 1H), 10.8 (s, 1H), 8.8 (d, 1H), 8.4 (s, 1H), 8.0 (s, 1H), 7.7 (br d, 4H), 7.5 (m, 2H), 7.0 (d, 1H), 2.6 (s, 6H); APCI−MS m/z 409 (M−H)−.
Source ID: ord-74a5a44d2e574e4aacfcb8679245ea1bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared analogously to Example 1c from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-2-indolinone and 4-aminobenzenesulphonic acid-dimethylamide.
Source ID: ord-269bd2e836f64ed6b0464e450ce23f23Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3f4664500e414b558e6294a874fd11eaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared analogously to Example 1c from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-2-indolinone and 4-aminobenzenesulphonic acid-dimethylamide.
Source ID: ord-269bd2e836f64ed6b0464e450ce23f23Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 4-oxazol-5-yl-aniline according to Procedure D: 1H NMR (DMSO-d6): δ 10.7 (s, 1H), 8.3 (s, 1H), 7.5 (s, 3H), 6.9 (d, 1H), 4.5 (s, 1H), 2.0 (s, 3H); APCI-MS m/z 247 (M+H)+. 5-Oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 3-methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure D: 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.3 (s, 1H), 7.5 (m, 3H), 6,8 (d, 1H), 3.5 (s, 2H); APCI-MS m/z 201 (M+H)+. 3-Ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure I: 1H NMR (DMSO-d6): δ 10.43 (s, 1H), 8.37 (s, 1H), 7.76 (s, 1H), 7.51 (m, 2H), 6.90, (d, 1H), 4.43 (q, 2H), 1.4 (t, 3H): APCI-MS m/z 255 (M−H)+. The title compound was prepared in 36% yield from 3-ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one and N,N-dimethyl-4-aminobenzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ 10.9(d, 1H), 10.8 (s, 1H), 8.8(d, 1H), 8.4 (s, 1H), 8.0 (s, 1H), 7.7 (br d, 4H), 7.5 (m, 2H), 7.0 (d, 1H), 2.6 (s, 6H); APCI-MS m/z 409 (M−H)−.
Source ID: ord-151991880f444937860fa569d72a7c58Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 4-oxazol-5-yl-aniline according to Procedure D: 1H NMR (DMSO-d6): δ 10.7 (s, 1H), 8.3 (s, 1H), 7.5 (s, 3H), 6.9 (d, 1H), 4.5 (s, 1H), 2.0 (s, 3H); APCI-MS m/z 247 (M+H)+. 5-Oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 3-methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure D: 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.3 (s, 1H), 7.5 (m, 3H), 6,8 (d, 1H), 3.5 (s, 2H); APCI-MS m/z 201 (M+H)+. 3-Ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure I: 1H NMR (DMSO-d6): δ 10.43 (s, 1H), 8.37 (s, 1H), 7.76 (s, 1H), 7.51 (m, 2H), 6.90, (d, 1H), 4.43 (q, 2H), 1.4 (t, 3H): APCI-MS m/z 255 (M−H)+. The title compound was prepared in 36% yield from 3-ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one and N,N-dimethyl-4-aminobenzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ 10.9(d, 1H), 10.8 (s, 1H), 8.8(d, 1H), 8.4 (s, 1H), 8.0 (s, 1H), 7.7 (br d, 4H), 7.5 (m, 2H), 7.0 (d, 1H), 2.6 (s, 6H); APCI-MS m/z 409 (M−H)−.
Source ID: ord-151991880f444937860fa569d72a7c58Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 4-oxazol-5-yl-aniline according to Procedure D: 1H NMR (DMSO-d6): δ 10.7 (s, 1H), 8.3 (s, 1H), 7.5 (s, 3H), 6.9 (d, 1H), 4.5 (s, 1H), 2.0 (s, 3H); APCI-MS m/z 247 (M+H)+. 5-Oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 3-methylsulfanyl-5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure D: 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.3 (s, 1H), 7.5 (m, 3H), 6,8 (d, 1H), 3.5 (s, 2H); APCI-MS m/z 201 (M+H)+. 3-Ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one was prepared from 5-oxazol-5-yl-1,3-dihydro-indol-2-one according to Procedure I: 1H NMR (DMSO-d6): δ 10.43 (s, 1H), 8.37 (s, 1H), 7.76 (s, 1H), 7.51 (m, 2H), 6.90, (d, 1H), 4.43 (q, 2H), 1.4 (t, 3H): APCI-MS m/z 255 (M−H)+. The title compound was prepared in 36% yield from 3-ethoxymethylene-5-oxazol-5-yl-1,3-dihydro-indol-2-one and N,N-dimethyl-4-aminobenzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ 10.9(d, 1H), 10.8 (s, 1H), 8.8(d, 1H), 8.4 (s, 1H), 8.0 (s, 1H), 7.7 (br d, 4H), 7.5 (m, 2H), 7.0 (d, 1H), 2.6 (s, 6H); APCI-MS m/z 409 (M−H)−.
Source ID: ord-151991880f444937860fa569d72a7c58Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared in 86% yield from compound (10) and 4-(N,N-dimethylsulfamoyl)phenylamine using the method described for Preparation 35. 1H-NMR (d6-DMSO, 500 MHz): δ 1.48 (s, 9H), 1.60 (s, 9H), 2.58 (s, 9H), 6.87 (d, J=0.63 Hz, 1H), 7.61 (d, J=9.14 Hz, 2H), 7.65 (s, 1H), 7.90 (d, J=8.83 Hz, 2H), 8.05 (d, J=0.63 Hz, 1H), 8.49 (d, J=0.63 Hz, 1H), 8.57 (d, J=0.95 Hz, 1H), 9.67 (s, 1H). described for Preparation 35
Source ID: ord-344eb6febafd48b5b2f5cc35706cdfd6PubChem References
These sources are listed in the compound's public database record.
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