5-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide → 5-(2-acetylthio-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 49533Notes

Reaction equation

HRID 49533 reaction equation
Br[CH:2]([C:26](=[O:28])[NH2:27])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)=[O:10].[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>O1CCCC1>[C:29]([S:31][CH:2]([C:26](=[O:28])[NH2:27])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)=[O:10])(=[O:32])[CH3:30]

Participants

4

Reactant 2

HCID 120946635-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamideHCID 23670855Potassium ethanethioate

Product 1

HCID 120946645-(2-acetylthio-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.00 g of 5-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 80 ml of tetrahydrofuran and 368 mg of potassium thioacetate under an atmosphere of argon, and the mixture was stirred for 6 hours at room temperature. Solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue, which was washed with water and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was crystallized from hexane-ethyl acetate, then the crystals were collected by filtration to obtain 904 mg of 5-(2-acetylthio-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as light brown crystals.

Workup

  1. distillationSolvent was distilled off under reduced pressure, and ethyl acetate
  2. additionwas added to the residue, which
  3. washwas washed with water and saturated brine in sequence
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationSolvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas crystallized from hexane-ethyl acetate
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-f6e5d696baad4eceb07ee81179ab7603
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Reaction notes

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