Ethanol → HCID 136060809, compound

HRID 1851520Notes

Reaction equation

HRID 1851520 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](=[S:21])[NH2:20])=[CH:15]2)(=[O:8])=[O:7].Cl[CH:23]([C:29](=O)[CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O)C.CN(C)C(=O)C>O>[CH3:30][C:29]1[N:20]=[C:19]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9][S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:7])=[O:8])[S:21][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 11858Ethyl 2-chloroacetoacetateHCID 31374DimethylacetamideHCID 57901763HCID 57901763, compound

Product 1

HCID 136060809HCID 136060809, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.50 g), ethyl 2-chloro-3-oxobutyrate (0.40 mL), ethanol (4 mL) and N,N-dimethylacetamide (4 mL) was stirred at 90° C. overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.47 g, yield 73%) was obtained as pale-yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 226-228° C.

Workup

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-061dd2de1f9e49c1b55500093d200d40
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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