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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851613Generated: October 29, 2026

Ammonia → 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

https://huagongshe.com/reaction/1851613

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantCitric AcidHCID 311—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidHCID 57476026—
SolventDimethylformamideHCID 6228—
Product6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamideHCID 5747602896.7%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a mixture of 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.83 g), 1H-1,2,3-benzotriazol-1-ol (0.38 g) and N,N-dimethylformamide (10 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide-hydrochloride (0.54 g) at room temperature, and the mixture was stirred at 50° C. for 20 min. The mixture was allowed to warm to room temperature, and 28% aqueous ammonia (0.30 mL) was added. The reaction mixture was stirred at room temperature for 1 hr and acidified with 10% aqueous citric acid solution. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.80 g, yield 96%) as colorless crystals. melting point>300° C. (decomposition).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957070B2
Source datasetuspto-grants-2015_02
ORD IDord-546a9368bdb84ad5a88e153a7fa0be29
Source noteuspto-grants-2015_02