Tetrahydrofuran → HCID 136060817, compound

HRID 1851527Notes

Reaction equation

HRID 1851527 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]1[S:20][CH:21]=[C:22]([C:24]([O:26]CC)=[O:25])[N:23]=1)=[CH:15]2)(=[O:8])=[O:7].[OH-].[Na+].O1CCCC1>CO>[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]1[S:20][CH:21]=[C:22]([C:24]([OH:26])=[O:25])[N:23]=1)=[CH:15]2)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136060800HCID 136060800, compound

Product 1

HCID 136060817HCID 136060817, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylate (0.30 g), 8N aqueous sodium hydroxide solution (0.3 mL), tetrahydrofuran (4 mL) and methanol (4 mL) was stirred at 60° C. for 1 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. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated to give the title compound (0.20 g, yield 71%) as yellow crystals. melting point>273° 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
  6. dissolutionThe obtained crystals were dissolved in tetrahydrofuran
  7. additiontreated with activated carbon
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-547c6861c20449eb8e83873d1202c507
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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