Tetrahydrofuran → HCID 57901672, compound

HRID 1851502Notes

Reaction equation

HRID 1851502 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24]([O:26]CC)=[O:25])=[CH:20]2)(=[O:13])=[O:12])(=[O:4])=[O:3].[OH-].[Na+].O1CCCC1>CO>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20]2)(=[O:12])=[O:13])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5195952HCID 5195952, compound

Product 1

HCID 57901672HCID 57901672, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 7-{[2-(methylsulfonyl)phenylsulfonyl]amino}-1H-indole-2-carboxylate (1.84 g), 8N aqueous sodium hydroxide solution (2.50 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at 60° C. for 2 hr. 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 (1.67 g, yield 97%) as yellow crystals. melting point>304° 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-5ed87a3495b0407db390b1d64901f284
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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