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

HRID 1634521

반응식

HRID 1634521 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-245da3ad5d894d1196cb37a4052f7e56
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506797B1

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