Sodium ethanethiolate → Ethyl 2-ethylthio-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoate

HRID 1634521Notes

Reaction equation

HRID 1634521 reaction equation
Br[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([C:17](=[O:30])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[S-:31][CH2:32][CH3:33].[Na+]>C(O)C>[CH2:32]([S:31][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([C:17](=[O:30])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:33]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 10874612Ethyl 2-bromo-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoate

Product 1

HCID 11059727Ethyl 2-ethylthio-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoateYield 353.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-bromo-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoate (1.00 g, 2.05 mmol; Example 37) and 56 ml of ethanol were mixed and, after sodium thioethoxide (268 mg, 2.55 mmol) was added under stirring, the mixture was refluxed for 1.5 hours. The reaction mixture was concentrated, water was added, and the solution was extracted with ethyl acetate. The extract was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=2:1 v/v) to obtain 3.4 g (43%) of the title compound as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=2:1 v/v)

Sources & evidence

ORD record
ord-245da3ad5d894d1196cb37a4052f7e56
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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