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

HRID 402330

반응식

HRID 402330 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
170 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-81783412adec46318b8f5c9a7909478f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742112B2

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