4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 178514735, compound

HRID 1264023Notes

Reaction equation

HRID 1264023 reaction equation
[O:1]1[C:5]2=[CH:6][C:7]3[C:8](=O)[C:9](=[O:13])[NH:10][C:11]=3[CH:12]=[C:4]2[O:3][CH2:2]1.[CH:15]1[C:20]([NH:21][NH2:22])=[CH:19][CH:18]=[C:17]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:16]=1.Cl>>[O:13]=[C:9]1[C:8](=[N:22][NH:21][C:20]2[CH:19]=[CH:18][C:17]([S:23]([NH2:26])(=[O:24])=[O:25])=[CH:16][CH:15]=2)[C:7]2[CH:6]=[C:5]3[O:1][CH2:2][O:3][C:4]3=[CH:12][C:11]=2[NH:10]1

Participants

3

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 156528332H,5H-[1,3]Dioxolo[4,5-f]indole-6,7-dione

Product 1

HCID 178514735HCID 178514735, compoundYield 55%

Procedure

The title compound was prepared from 5H-[1,3]dioxolo[4,5-f]indole-6,7-dione (Lackey and Stembach, Synthesis 1993, 993-7) and 4-sulfonamidophenylhydrazine hydrochloride in 55% yield as an orange crystalline solid following Procedure G: mp>220° C.; 1H NMR (DMSO-d6): δ 12.63 (s, 1H), 10.89 (s, 1H), 7.73 (d, J=7 Hz, 2H), 7.50 (d, J=7 Hz, 2H), 7.22 (s, 2H), 7.13 (s, 1H), 6.56 (s, 1H), 6.00 (s, 2H), Anal. Calcd for C15H12N4O5S: C, 50.00; H, 3.36; N, 15.55. Found: C, 50.08; H, 3.35; N, 15.49.

Sources & evidence

ORD record
ord-fc4dcd40e438451b9437d432d3fbcf99
Source dataset
uspto-grants-2003_04
Patent number
US06541503B2

Reaction notes

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