4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 178517011, compound

HRID 840865Notes

Reaction equation

HRID 840865 reaction equation
NC1C=C2C(=CC=1)NN=C2Cl.[Cl:12][C:13]1[C:21]2[C:20]3[C:22](=[O:26])[C:23](=[O:25])[NH:24][C:19]=3[CH:18]=[CH:17][C:16]=2[NH:15][N:14]=1.[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>>[Cl:12][C:13]1[C:21]2[C:20]3[C:22](=[O:26])[C:23](=[O:25])[NH:24][C:19]=3[CH:18]=[CH:17][C:16]=2[NH:15][N:14]=1.[Cl:12][C:13]1[C:21]2[C:20]3[C:22](=[N:34][NH:33][C:32]4[CH:31]=[CH:30][C:29]([S:35]([NH2:38])(=[O:36])=[O:37])=[CH:28][CH:27]=4)[C:23](=[O:25])[NH:24][C:19]=3[CH:18]=[CH:17][C:16]=2[NH:15][N:14]=1

Participants

5

Reactant 3

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 178507360HCID 178507360, compoundHCID 178517011HCID 178517011, compound

Product 2

HCID 178514738HCID 178514738, compoundHCID 178517011HCID 178517011, compoundYield 38%

Procedure

1-Chloro-3,6-dihydro-pyrrolo[3,2-e]indazole-7,8-dione was prepared from 5-amino-3-chloroindazole according to Procedure A in 38% yield: 1H NMR (DMSO-d6): δ7.08 (d, J=7.9 Hz, 1H), 7.92 (d, J=7.9 Hz, 1H), 10.95 (s, 1H), 13.70 (s, 1H). Condensation of 1-chloro-3,6-dihydro-pyrrolo[3,2-e]indazole-7,8-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 45% yield: 1H NMR (DMSO-d6): δ7.11 (d, J=8.8 Hz, 1H), 7.26 (s, 2H), 7.51 (d, J=8.8 Hz, 1H), 7.64 (d, J=8.8 Hz, 2H), 7.82 (d, J=8.8 Hz, 2H), 11.17 (s, 1H), 13.25 (s, 1H), 13.41 (s, 1H): APCI−MS m/z 389/391 (M−H)−. Anal. Calcd for C15H11CIN6O3S: C, 44.86, H, 3.06; N, 20.93; S, 7.98. Found C, 45.02, H, 3.31; N, 20.92; S, 7.77.

Sources & evidence

ORD record
ord-97063bec3f164dc28014b2efe705ed20
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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