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

HRID 644534ノート

反応式

HRID 644534 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 674850037-Fluoro-1-phenyl-5-trifluoromethylbenzimidazole収率 87%

反応条件

温度
110 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-32e72dcd683c45e2af50cf65922a16fc
出典データセット
uspto-grants-2010_04
特許番号
US07700638B2

反応ノート

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