Dimethyl Sulfoxide → 2-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole

HRID 402330

反応式

HRID 402330 の反応式
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[SH:13].[F:14][C:15]1[CH:22]=[N:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.C(N(C(C)C)C(C)C)C.CS(C)=O>O>[F:14][C:15]1[CH:22]=[N:21][CH:20]=[CH:19][C:16]=1[C:17]1[S:13][C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:3]=2[N:2]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochlorideHCID 27630033-Fluoroisonicotinaldehyde

生成物 1

HCID 671137612-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole収率 60.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
170 °C

実験手順

A mixture of 2.3 g of 2-amino-4-(trifluoromethyl)-benzenethiol hydrochloride, 1.25 g of 3-fluoroisonicotinaldehyde, 1.29 g of N-ethyldiisopropylamine and 10 ml of DMSO was stirred for 5 hours at 170° C. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate twice. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 1.79 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole (hereinafter, referred to as the present compound 1).

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe resultant mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-81783412adec46318b8f5c9a7909478f
出典データセット
uspto-grants-2014_06
特許番号
US08742112B2

関連ノート

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