6-Aminobenzothiazole → 6H-thiazolo[5,4-e]indole-7,8-dione

HRID 840883Notes

Reaction equation

HRID 840883 reaction equation
N[C:2]1C=CC2N=CSC=2C=1.[S:11]1[C:22]2[C:14](=[CH:15][CH:16]=[C:17]3[C:21]=2[C:20](=[O:23])[C:19](=[O:24])[NH:18]3)[N:13]=[CH:12]1.[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>O>[S:11]1[C:22]2[C:14](=[CH:15][CH:16]=[C:17]3[C:21]=2[C:20](=[O:23])[C:19](=[O:24])[NH:18]3)[N:13]=[CH:12]1.[CH3:2][NH:36][S:33]([C:27]1[CH:26]=[CH:25][C:30]([NH:31][N:32]=[C:20]2[C:21]3[C:17](=[CH:16][CH:15]=[C:14]4[C:22]=3[S:11][CH:12]=[N:13]4)[NH:18][C:19]2=[O:24])=[CH:29][CH:28]=1)(=[O:34])=[O:35]

Participants

6

Reactant 3

HCID 682886-AminobenzothiazoleHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 117457566H-thiazolo[5,4-e]indole-7,8-dione

Product 2

HCID 117457566H-thiazolo[5,4-e]indole-7,8-dioneHCID 178486273N-methyl-4-[2-(7-oxopyrrolo[2,3-g][1,3]benzothiazol-8-yl)hydrazinyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6H-1-Thia-3,6-diaza-as-indacene-7,8-dione was prepared from 6-aminobenzothiazole according to Procedure A: 1H NMR (DMSO-d6): δ7.10 (d, J=8.4 Hz, 1H), 8.31 (d, J=8.5 Hz, 1H), 9.35 (s, 1H), 11.19 (s, 1H); ESI−MS m/z 204 (M)−. The title compound was prepared from 6H-1-thia-3,6-diaza-as-indacene-7,8-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G: mp>260° C.; 1H NMR (DMSO-d6): δ2.39 (d, J=5.1 Hz, 3H), 7.12 (d, J=8.4 Hz, 1H), 7.32 (q, J=5.1 Hz, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.7 Hz, 2H), 7.99 (d, J=8.6 Hz, 1H), 9.30 (s, 1H), 11.26 (s, 1H), 12.69 (s, 1H); APCI−MS m/z 387 (M)−. Anal. Calcd for C16H13N5O3S2.0.33 H2O: C, 48.85; H, 3.50; N, 17.80; S, 16.30. Found: C, 48.89; H, 3.40; N, 17.67; S, 16.23.

Sources & evidence

ORD record
ord-4b4baad977a94b828936715560453853
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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