4-(Methylsulfonyl)aniline → HCID 10911220, compound

HRID 840840Notes

Reaction equation

HRID 840840 reaction equation
CS(C1C=CC(N)=CC=1)(=O)=O.[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26])(=[O:15])=[O:14].[CH:27]1[C:32]([NH:33][NH2:34])=[CH:31][CH:30]=[C:29]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:28]=1.Cl>>[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26])(=[O:15])=[O:14].[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[N:34][NH:33][C:32]1[CH:31]=[CH:30][C:29]([S:35]([NH2:38])(=[O:36])=[O:37])=[CH:28][CH:27]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 796174-(Methylsulfonyl)anilineHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 10911220HCID 10911220, compound

Product 2

HCID 10911220HCID 10911220, compoundHCID 178504651HCID 178504651, compound

Procedure

5-Methylsulfonyl-1H-indole-2,3-dione was prepared from 4-methylsulfonylaniline according to Procedure A: 1H NMR (DMSO-d6): δ3.21 (s, 3H), 7.07(d, J=8.3 Hz, 1H), 7.92 (d, J=1.7 Hz, 1H), 8.05 (dd, J=8.2, 2.0 Hz, 1H), 11.46 (s, 1H); APCI−MS m/z 225 (M)−. The title compound was prepared from 5-methylsulfonyl-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G: mp>250° C.; 1H NMR (DMSO-d6): δ3.20 (s, 3H), 7.11 (d, J=8.3 Hz, 1H), 7.26 (s, 2H), 7.65 (d, J=8.9 Hz, 2H), 7.78 (d, J=8.7 Hz, 2H), 7.79 (dd, J=8.2, 1.9 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 11.54 (s, 1H), 12.75 (s, 1H); APCI−MS m/z 394 (M)−. Anal. Calcd for C15H14N4O5S2.0.9H2O: C, 43.87; H, 3.88; N, 13.64; S, 15.62. Found: C, 43.96; H, 3.80; N, 13.58; S, 15.67.

Sources & evidence

ORD record
ord-4fc21fb6443f4b1ba99d8424b7b12b6b
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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