4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 178517012, compound

HRID 840864Notes

Reaction equation

HRID 840864 reaction equation
[NH:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[C:10](=[O:13])[C:9](=[O:14])[NH:8]3)[N:3]=[N: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>>[NH:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[C:10](=[O:13])[C:9](=[O:14])[NH:8]3)[N:3]=[N:2]1.[O:14]=[C:9]1[C:10](=[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:11]2[C:7](=[CH:6][CH:5]=[C:4]3[C:12]=2[N:1]=[N:2][NH:3]3)[NH:8]1

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 178517012HCID 178517012, compound

Product 2

HCID 178514739HCID 178514739, compoundHCID 178517012HCID 178517012, compoundYield 56%

Procedure

1,6-Dihydro-1,2,3,6-tetraaza-as-indacene-7,8-dione was prepared according to Procedure A in 56% yield: 1H NMR (DMSO-d6): δ6.93 (d, J=8.6 Hz, 1H), 8.32 (d, J=8.6 Hz, 1H), 11.14 (s, 1H); APCI−MS m/z 189 (M+1)+. Condensation of 1,6-dihydro-1,2,3,6-tetraaza-as-indacene-7,8-dione with 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 15% yield: 1H NMR (DMSO-d6): δ7.06 Z (d, J=8.4 Hz, 1H), 7.24 E (d, J=8.4 Hz, 1H), 7.30 Z (s, 2H), 7.30 E (s, 2H), 7.55 E (d, J=8.5 Hz, 2H), 7.82 Z (d, J=8.5 Hz, 2H), 7.82 E (d, J=8.5 Hz,1H), 7.90 E (d, J=8.7 Hz, 2H), 7.90 Z (d, J=8.8 Hz, 2H), 7.98 Z (d, J=8.4 Hz,1H), 10.86 E (s,1H), 11.35 Z (s, 1H), 12.87 Z (s, 1H), 12.95 E (s, 1H), 16.00 Z (s, 1H), 16.25 E (s, 1H); APCI−MS m/z 356 (M−H)−. Anal. Calcd for C14H11N7O3S.H2O: C, 44.80, H, 3.49; N, 26.12; S, 8.54. Found C, 44.72, H, 3.46; N, 26.05; S, 8.48.

Sources & evidence

ORD record
ord-2de5a907861a44e9978b5310c6d10c3c
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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