Aniline → 7-Fluoro-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644534노트

반응식

HRID 644534 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[N+:20]([O-])=O.Cl[CH2:24]Cl>>[F:15][C:14]1[C:9]2[N:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:24]=[N:20][C:10]=2[CH:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:13]=1

참가 물질

4

반응물 3

HCID 6115AnilineHCID 6344DichloromethaneHCID 27370313,4-Difluoro-5-nitrobenzotrifluoride

생성물 1

HCID 674850037-Fluoro-1-phenyl-5-trifluoromethylbenzimidazole수율 87%

반응 조건

온도
110 °C

실험 절차

A mixture of aniline (1.12 ml, 12.3 mmol) and 2,3-difluoro-1-nitro-5-trifluoromethylbenzene (2.8 g, 12.3 mmol) was heated at 110° C. for 24 h. Dichloromethane was added and the resulting precipitate filtered off. The filtrate was concentrated under reduced pressure then redissolved in ethyl acetate. 10% Palladium on carbon (0.5 g, Degussa) was added and the resulting suspension hydrogenated at 5 bar for 1 h. The reaction mixture was filtered through celite, washed with ethyl acetate and, the filtrate concentrated under reduced pressure. Formic acid (10 mL) was added and the mixture heated at 110° C. for 24 h. Concentration under reduced pressure gave 7-fluoro-1-phenyl-5-trifluoromethylbenzimidazole as a purple solid (3.0 g, 87%) m/z, 281.0 (M+H)+.

후처리

  1. filtrationthe resulting precipitate filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthen redissolved in ethyl acetate
  4. addition10% Palladium on carbon (0.5 g, Degussa) was added
  5. filtrationThe reaction mixture was filtered through celite
  6. washwashed with ethyl acetate
  7. concentrationthe filtrate concentrated under reduced pressure
  8. additionFormic acid (10 mL) was added
  9. temperaturethe mixture heated at 110° C. for 24 h
  10. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-32e72dcd683c45e2af50cf65922a16fc
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700638B2

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