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

Participants

Role	Name	HCID	Charge
Reactant	6-Aminobenzothiazole	HCID 68288	—
Reactant	4-Hydrazinylbenzenesulfonamide hydrochloride	HCID 2794567	—
Reactant	6H-thiazolo[5,4-e]indole-7,8-dione	HCID 11745756	—
Solvent	Water	HCID 962	—
Product	6H-thiazolo[5,4-e]indole-7,8-dione	HCID 11745756	—
Product	N-methyl-4-[2-(7-oxopyrrolo[2,3-g][1,3]benzothiazol-8-yl)hydrazinyl]benzenesulfonamide	HCID 178486273	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06369086B1
Source dataset	uspto-grants-2002_04
ORD ID	ord-4b4baad977a94b828936715560453853
Source note	uspto-grants-2002_04