Thionyl Chloride → n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamide

HRID 1017428ノート

反応式

HRID 1017428 の反応式
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:26][NH:27][CH:28]1[CH2:30][CH2:29]1>ClCCl.CN(C)C=O>[F:21][C:22]([F:38])([F:39])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=1)[CH2:26][N:27]([CH:28]1[CH2:29][CH2:30]1)[C:13](=[O:15])[C:12]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:16])=[CH:8][CH:9]=[N:10][CH:11]=1

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 158874064-(2-Methylphenyl)nicotinic acidHCID 15887407(3,5-Bistrifluoromethylbenzyl)cyclopropylamine

生成物 1

HCID 9806536n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamide収率 58.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 106 mg (0.5 mmol) 4-o-tolyl-nicotinic acid in 5 ml dichloromethane and 2 drops N,N-dimethylformamide was stirred with 0.1 ml (1.4 mmol) thionyl chloride for 1.5 h at room temperature. The solvent was removed and the residue was taken up in 5 ml dichloromethane and 0.3 ml triethylamine. After the addition of 155 mg (0.55 mmol) (3,5-bis-trifluoromethyl-benzyl)-cyclopropyl-amine the mixture was stirred at room temperature for 1 h and washed twice with water. The organic layer was dried (magnesium sulfate) and evaporated. The crude oil was subjected to column chromatography to give 140 mg (58%) of the title compound as an oil.

後処理

  1. customThe solvent was removed
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. customevaporated

出典と根拠

ORDレコード
ord-b81ce9eeca524e38991e6f35bf2495e1
出典データセット
uspto-grants-2002_11
特許番号
US06479483B2

反応ノート

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