Benzenesulfonamide, 3-amino- → HCID 178514716, compound

HRID 1391493Notes

Reaction equation

HRID 1391493 reaction equation
O/[CH:2]=[C:3]1\[C:4](=[O:12])[NH:5][C:6]2[C:11]\1=[CH:10][CH:9]=[CH:8][CH:7]=2.[NH2:13][C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>CCO>[O:12]=[C:4]1[NH:5][C:6]2[C:11](/[C:3]/1=[CH:2]/[NH:13][C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:21])=[O:22])[CH:17]=[CH:18][CH:19]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 178517101HCID 178517101, compound

Product 1

HCID 178514716HCID 178514716, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.161 g (1.0 mmol) of (3Z)-3-(hydroxymethylene)-1,3-dihydro-2H-indol-2-one 1,2 and 0.180 g (1.05 mmol) of 3-aminobenzene-1-sulfonamide in 5 ml of EtOH was heated to 80° C. for 45 min. After cooling to ambient temperature, the solid was collected by vacuum filtration and air dried to afford 3-{[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-methyl]amino}benzenesulfonamide as a yellow solid (0.25 g, 79%). mp>250° C.; 1H NMR (DMSO-d6): 6.82 (d, J=7.7 Hz, 1H), 6.87-6.94 (m, 1H), 6.97-7.30 (m, 1H), 7.35 (s, 2H), 7.42-7.47 (m, 1H), 7.50-7.63 (m, 3H), 7.75 (t, J=1.8 Hz, 1H), 8.59 (d, J=12.1 Hz, 1H), 10.53 (s, 1H), 10.85 (d, J=12.3 Hz, 1H); APCI-MS: m/z 316 (m+H)+. Anal. Calcd for C15H13N3O3S: C, 57.13; H, 4.16; N, 13.32; S, 10.17. Found: C, 57.01; H, 4.23; N, 13.30; S, 10.11.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe solid was collected by vacuum filtration and air
  3. customdried

Sources & evidence

ORD record
ord-d7d067efe55b48089a7dd3bd0bf35d7f
Source dataset
uspto-grants-2008_03
Patent number
US07338966B2

Reaction notes

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