3-Aminobenzamide → HCID 11116821, compound

HRID 840822Notes

Reaction equation

HRID 840822 reaction equation
NC1C=CC=C(C(N)=O)C=1.[NH:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]([NH2:22])=[O:21])[C:14]=2[C:13](=[O:23])[C:12]1=[O:24].[CH:25]1[C:30]([NH:31][NH2:32])=[CH:29][CH:28]=[C:27]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:26]=1.Cl>>[NH:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]([NH2:22])=[O:21])[C:14]=2[C:13](=[O:23])[C:12]1=[O:24].[O:24]=[C:12]1[C:13](=[N:32][NH:31][C:30]2[CH:29]=[CH:28][C:27]([S:33](=[O:35])(=[O:34])[NH2:36])=[CH:26][CH:25]=2)[C:14]2[C:15]([C:20]([NH2:22])=[O:21])=[CH:16][CH:17]=[CH:18][C:19]=2[NH:11]1

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 11116821HCID 11116821, compound

Product 2

HCID 11116821HCID 11116821, compoundYield 3%HCID 178513602HCID 178513602, compound

Procedure

1H-Indole-2,3-dione-4-carboxamide was prepared from aniline-3-carboxamide according to Procedure A in 3% yield: 1H NMR (DMSO-d6): δ7.17 (d, J=8.1 Hz, 1H), 7.32 (d, J=8.1 Hz, 1H), ), 7.56 (t, J=8.1 Hz, 1H), 8.02 (bs, 2H), 11.86 (bs, 1H); APCI+MS m/z 191 (M+1)−. Condensation of 1H-indole-2,3-dione-4-carboxamide with 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 31% yield: 1H NMR (DMSO-d6): δ7.11 (d, J=8.3 Hz, 1H), 7.18 (s, 2H), 7.27 (d, J=8.8 Hz, 2H), 7.32 (d, J=7.0 Hz, 1H), 7.51 (d, J=7.4 Hz, 1H), 7.75 (d, J=8.8 Hz, 2H), 8.0 (bs, 2H), 10.40 (s, 1H), 10.80 (s, 1H); APCI−MS m/z 359 (M)−. Anal. Calcd for C15H13N5O4S.0.12H2O: C, 49.83, H, 3.69; N, 19.37; S, 8.86. Found C, 49.71, H, 3.71; N, 19.32; S, 8.84.

Sources & evidence

ORD record
ord-f5fdeef687a0438aa2e1933cbe43747d
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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