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

HRID 1949153ノート

反応式

HRID 1949153 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88758ace43f74dcdb759344c5a002fd1
出典データセット
uspto-grants-2013_03
特許番号
US08399673B2

反応ノート

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