Thioacetamide → HCID 15231189, compound

HRID 2353429Notes

Reaction equation

HRID 2353429 reaction equation
Br[CH:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:4][C:3]1=[O:17].[C:18](=[S:21])([NH2:20])[CH3:19]>CN(C)C=O.C(OCC)(=O)C>[CH3:19][C:18]1[S:21][CH:2]2[CH2:6][N:5]([S:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)(=[O:9])=[O:8])[CH2:4][C:3]2([OH:17])[N:20]=1

Participants

5

Reactant 2

HCID 2723949ThioacetamideHCID 152311954-Bromo-1-(4-methylbenzene-1-sulfonyl)pyrrolidin-3-one

Product 1

HCID 15231189HCID 15231189, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 4-bromo-1-[(4-methylphenyl)sulfonyl]pyrrolidin-3-one (159 mg) (W.-J Kim, et al., Heterocycles, 1995, 41, 1389-1398) in 2 mL of N,N-dimethylformamide was added ethanethioamide (38 mg) and the reaction mixture heated to 50° C. for 2 h. The mixture was cooled to ambient temperature and diluted with a mixture of ethyl acetate/saturated aqueous sodium bicarbonate solution (1:1, 20 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3×10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, evaporated in vacuo The product was used without further purification. LC/MS 313.1 (M+1).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo The product
  7. customwas used without further purification

Sources & evidence

ORD record
ord-22b9a7fb71db4beda194929830ef68a4
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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