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

HRID 339526

반응식

HRID 339526 반응식
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:14][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[S:28][C:29]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:30]=4[N:31]=3)=[CH:25][CH:26]=2)=[O:11])=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 37639014-(2,2,2-Trifluoroethoxy)benzoic acid

생성물 1

HCID 673118514-(2,2,2-Trifluoroethoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide수율 91%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

A mixture of 4-(2,2,2-trifluoroethoxy)benzoic acid (0.30 g, 1.35 mmol) and thionyl chloride (0.32 g, 2.72 mmol) in chloroform (5 ml) was heated under reflux for 4 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 (0.34 g, 1.35 mmol) in dry pyridine (15 ml) to give the title compound (0.56 g, 91%) as a pale yellow solid after work-up.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4 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-d6518cb0a1b843b49c336e9e89e2d4b3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895313B2

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