Benzonitrile, 4-(trifluoromethyl)- → HCID 178504795、化合物

HRID 1352961ノート

反応式

HRID 1352961 の反応式
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C[Al](C)C.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:19]=[CH:20][C:21]([C:22](=[NH:23])[NH:9][C:8]2[CH:10]=[CH:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:24][CH:25]=1

参加物

6

反応物 3

HCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 796174-(Methylsulfonyl)anilineHCID 16682925Trimethylaluminum

生成物 1

HCID 178504795HCID 178504795、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 6212Chloroform溶媒

実験手順

To a suspension of 4-(methylsulfonyl)aniline (10 mmol) in toluene (100 mL), trimethylaluminum (2M solution in toluene, 15 mmol) is added over 15 minutes. The reaction mixture is warmed to room temperature and stirred for 2.5 hours. A solution of 4-trifluoromethylbenzonitrile (20 mmol) in toluene (50 mL) is added over 10 minutes and the reaction mixture is heated to 80–85° C. After 20 hours, the reaction mixture is cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue is washed with a mixture of methylene chloride/methanol (2/1). The combined filtrates are concentrated in vacuo and the resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL). The intermediate is filtered and washed with more of hexane/ether (2/1). The pale yellow solid 4-(trifluoromethyl)-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification.

後処理

  1. additionis added over 15 minutes
  2. temperaturethe reaction mixture is heated to 80–85° C
  3. waitAfter 20 hours
  4. temperaturethe reaction mixture is cooled to room temperature
  5. filtrationAfter filtration
  6. washthe residue is washed with a mixture of methylene chloride/methanol (2/1)
  7. concentrationThe combined filtrates are concentrated in vacuo
  8. stirringthe resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL)
  9. filtrationThe intermediate is filtered
  10. washwashed with more of hexane/ether (2/1)
  11. customThe pale yellow solid 4-(trifluoromethyl)-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification

出典と根拠

ORDレコード
ord-8fc65624451145b8a3c439ccd5286b1c
出典データセット
uspto-grants-2007_05
特許番号
US07220770B2

反応ノート

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