Dimethylacetamide → HCID 57901574, compound

HRID 1851535Notes

Reaction equation

HRID 1851535 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.Br[CH:24]([CH:32]=O)[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].CN(C)C(=O)C>O>[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]1[S:14][C:24]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:32][N:13]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 574759607-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamideHCID 71369674Ethyl 4-bromo-5-oxopentanoate

Product 1

HCID 57901574HCID 57901574, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (4.00 g), ethyl 4-bromo-5-oxopentanoate (3.80 g) and N,N-dimethylacetamide (25 mL) was stirred at 90° 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 (3.79 g, yield 70%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:3, volume ratio). melting point 126-127° 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-e91e6e240da44b5e8cafa74971a3714b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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