Dimethylacetamide → HCID 57901779, compound

HRID 1851610Notes

Reaction equation

HRID 1851610 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].Br[CH:23]([CH:26]=O)[CH:24]=[O:25].CN(C)C(=O)C>O>[OH:25][CH2:24][C:23]1[S:21][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])=[N:20][CH:26]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 57901763HCID 57901763, compound

Product 1

HCID 57901779HCID 57901779, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (1.12 g), bromomalonaldehyde (0.90 g) and N,N-dimethylacetamide (15 mL) was stirred at 90° C. for 1 hr. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. To a mixture of the obtained crystals, tetrahydrofuran (10 mL) and methanol (10 mL) was added sodium borohydride (0.13 g) at 0° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.70 g, yield 60%) was obtained as pale-yellow crystals from a fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). melting point 209-210° C.

Workup

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried
  4. additionTo a mixture of the obtained crystals, tetrahydrofuran (10 mL) and methanol (10 mL)
  5. additionwas added sodium borohydride (0.13 g) at 0° C.
  6. stirringthe mixture was stirred at the same temperature for 1 hr
  7. additionTo the reaction mixture was added 10% aqueous citric acid solution
  8. additionwas added
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a520fb034ecb404980e6295443e91be0
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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