4-(1,2,4-Triazol-1-yl)aniline → 5-[1,2,4]Triazol-1-yl-1H-indole-2,3-dione

HRID 840837Notes

Reaction equation

HRID 840837 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[N:13]1([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[C:21]3=[O:28])[CH:17]=[N:16][CH:15]=[N:14]1.[NH:29]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:40][CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=1)[NH2:30]>>[N:13]1([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[C:21]3=[O:28])[CH:17]=[N:16][CH:15]=[N:14]1.[CH3:41][NH:40][S:37]([C:34]1[CH:35]=[CH:36][C:31]([NH:29][N:30]=[C:21]2[C:8]3[C:9](=[CH:10][CH:11]=[C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)[CH:7]=3)[NH:12][C:22]2=[O:27])=[CH:32][CH:33]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 7358264-(1,2,4-Triazol-1-yl)anilineHCID 154068074-hydrazino-N-methyl-phenylsulfonamideHCID 219562215-[1,2,4]Triazol-1-yl-1H-indole-2,3-dione

Product 2

HCID 219562215-[1,2,4]Triazol-1-yl-1H-indole-2,3-dioneYield 6%HCID 178486274HCID 178486274, compound

Procedure

5-[1,2,4]Triazol-1-yl-1H-indole-2,3-dione was prepared from 4-[1,2,4]-triazol-1-yl-phenylamine according to Procedure A in 6% yield: 1H NMR (DMSO-d6): δ7.04 (d, J=8.4Hz, 1H), 7.97 (d, J=2.2 Hz, 1H), 8.01 (dd, J=2.2, 8.4 Hz, 1H), 8.20 (s, 1H), 9.26 (s, 1H), 11.19 (bs, 1H); APCI−MS m/z 215 (M+1)+. Condensation of 5-[1,2,4]triazol-1-yl-1H-indole-2,3-dione with 4-hydrazino-N-methyl-phenylsulfonamide according to Procedure G gave the title compound in 86% yield: 1H NMR (DMSO-d6): δ2.38 (d, J=5.0 Hz, 3H), 7.05 (d, J=8.4 Hz, 1H), 7.30 (q, J=5.0 Hz, 1H), 7.65 (d, J=8.7 Hz, 2H), 7.72 (d, J=8.7 Hz, 3H), 8.01 (s, 1H), 8.20 (s, 1H), 9.23 (s, 1H), 11.27 (s, 1H), 12.80 (s, 1H); Anal. Calcd for C16H15N7O3S.1.3H2O: C, 48.52, H, 4.22; N, 23.30; S, 7.62. Found C, 48.53, H, 4.25; N, 23.17; S, 7.55.

Sources & evidence

ORD record
ord-48242d2363ae4825bd3c78e27bae3c97
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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