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Tetrahydrofuran → 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 1851612
Notes
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Reaction equation

HRID 1851612 reaction equation
[Cl:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:20]([O:22]CC)=[O:21])[NH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1>CO>[Cl:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:20]([OH:22])=[O:21])[NH:8]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57476027ethyl 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 574760266-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (1.00 g), 4N aqueous sodium hydroxide solution (2.3 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated and acidified with 10% aqueous citric acid solution. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.88 g, yield 95%) as colorless crystals. melting point>290° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe resulting crystals were filtrated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b80aef68e3334a7d8c6648d995c3f993
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957070B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes