Potassium Carbonate → 2-(2-(Phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 1949153노트

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HRID 1949153 반응식
C([O-])([O-])=O.[K+].[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[N:21]=1>CC(C)=O>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:26]=3)[N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 4470932-(Phenylsulfonyl)ethanethiolHCID 866453392-Chloro-6-(trifluoromethyl)quinoline-3-carboxylic acid

생성물 1

HCID 671336762-(2-(Phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid수율 72%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
70 °C

실험 절차

206 mg (1.5 mmol) K2CO3 and 303 mg (1.5 mmol) 2-(phenylsulfonyl)ethanethiol were added to a solution of 827 mg (1.0 mmol) 2-chloro-6-(trifluoromethyl)quinoline-3-carboxylic acid (precursor VVV03) in acetone (3 ml) and the mixture was heated for 5 h at 70° C. Then it was filtered and the filtrate was concentrated to small volume under vacuum. The residue was dissolved in water and acidified with a 1N hydrochloric acid. It was then extracted with EE and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. Crystallisation (DCM/hexane) of the residue yielded 316 mg (0.7 mmol, 72%) 2-(2-(phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid.

후처리

  1. filtrationThen it was filtered
  2. concentrationthe filtrate was concentrated to small volume under vacuum
  3. dissolutionThe residue was dissolved in water
  4. extractionIt was then extracted with EE
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customCrystallisation (DCM/hexane) of the residue

출처 및 근거

ORD 기록
ord-88758ace43f74dcdb759344c5a002fd1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399673B2

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