Dimethylacetamide → HCID 59136021, compound

HRID 1851625Notes

Reaction equation

HRID 1851625 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]([S:19]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)(=[O:21])=[O:20])[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][C:13]([C:16](=[S:18])[NH2:17])=[CH:12]2)[CH3:2].Br[CH:28]([CH:31]=O)[CH:29]=[O:30].CN(C)C(=O)C.[BH4-].[Na+]>C(OCC)(=O)C.O.O1CCCC1.CO>[CH2:1]([O:3][CH2:4][CH2:5][N:6]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][C:13]([C:16]1[S:18][C:28]([CH2:29][OH:30])=[CH:31][N:17]=1)=[CH:12]2)[S:19]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:21])[CH3:2]

Participants

9

Reactant 4

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 4311764Sodium borohydrideHCID 57475964HCID 57475964, compound

Product 1

HCID 59136021HCID 59136021, compoundYield 29.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

7-[(2-Ethoxyethyl) (2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (3.00 g), bromomalonaldehyde (2.32 g) and N,N-dimethylacetamide (50 mL) were stirred at 95° C. for 3 hr. The reaction mixture was diluted with ethyl acetate and water, and the ethyl acetate layer was washed successively with saturated brine and aqueous sodium bicarbonate, dried over magnesium sulfate and filtrated. The filtrate was concentrated, subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate-hexane (1:1) to give a solid. The solid was dissolved in tetrahydrofuran (50 mL) and methanol (20 mL), sodium borohydride (176 mg) was added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtrated. The filtrate was concentrated, subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate-hexane (2:1) to give the title compound (1.00 g, yield 29%) as an amorphous form.

Workup

  1. washthe ethyl acetate layer was washed successively with saturated brine and aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. washeluted with a mixture of ethyl acetate-hexane (1:1)
  6. customto give a solid
  7. washwashed with saturated brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltrated
  10. concentrationThe filtrate was concentrated
  11. washeluted with a mixture of ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-ca3317fad9be4dfabe2fcec8294d2822
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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