1,3-Dichloroacetone → HCID 136060814, compound

HRID 1851538Notes

Reaction equation

HRID 1851538 reaction equation
[CH3:1][N:2]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[Cl:23][CH2:24][C:25](=O)[CH2:26]Cl.CN(C)C(=O)C>O>[Cl:23][CH2:24][C:25]1[N:13]=[C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])[S:14][CH:26]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 31374DimethylacetamideHCID 574759607-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

Product 1

HCID 136060814HCID 136060814, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.46 g), 1,3-dichloro-2-propanone (0.33 g) and N,N-dimethylacetamide (6 mL) was stirred at 80° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.45 g, yield 85%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 153-154° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee841723abf84378b8ba5cbff2991f5f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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