Tetrahydrofuran → HCID 57476168, compound

HRID 1851425Notes

Reaction equation

HRID 1851425 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15]2)(=[O:8])=[O:7].[OH-].[Na+].O1CCCC1>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15]2)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 4076385HCID 4076385, compound

Product 1

HCID 57476168HCID 57476168, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (7.81 g), 8N aqueous sodium hydroxide solution (11.0 mL), tetrahydrofuran (20 mL) and ethanol (30 mL) was stirred at 50° C. overnight. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (7.00 g, yield 97%) as colorless crystals. melting point>268° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5eabefcee2774c60b223f78641409d8c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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