Thionyl Chloride → 4-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide

HRID 339528노트

반응식

HRID 339528 반응식
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]3[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=3[N:33]=2)=[CH:25][CH:24]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:16][C:2]([F:1])([F:17])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[S:30][C:31]4[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=4[N:33]=3)=[CH:27][CH:28]=2)=[O:13])=[CH:14][CH:15]=1

참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 223614014-(4,4,4-Trifluorobutoxy)benzoic acid

생성물 1

HCID 673125284-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide수율 87.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

A mixture of 4-(4,4,4-trifluorobutoxy)benzoic acid (0.20 g, 0.806 mmol) and thionyl chloride (0.42 g, 3.54 mmol) in chloroform (5 ml) was heated under reflux for 8 h. The reaction mixture was cooled to room temperature and the excess reagent and solvent was removed under reduced pressure to give the crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude acid chloride and 2-(4-aminophenyl)-6-methoxybenzothiazole (0.206 g, 0.806 mmol) in dry pyridine (10 ml) to give the title compound (0.343 g, 87%) as a colourless solid after work-up.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. customthe excess reagent and solvent was removed under reduced pressure
  4. customto give the crude acid chloride
  5. customThe amide was prepared

출처 및 근거

ORD 기록
ord-d06e25573834415e9dabda2a1e5b6968
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895313B2

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