Triethylamine → N-cyclohexyl-N-methyl-2-nitrobenzamide

HRID 852233ノート

反応式

HRID 852233 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH:13]1(CN)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:21]([N:23](CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH:13]1([N:23]([CH3:21])[C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 76688Cyclohexanemethylamine

生成物 1

HCID 799283N-cyclohexyl-N-methyl-2-nitrobenzamide収率 74.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 2-nitrobenzoyl chloride (1.0 g, 5.4 mmol) in dichloromethane (1 ml) was added dropwise to a stirred solution of cyclohexylmethylamine (0.068 g, 6 mmol), triethylamine (1.12 ml, 8 mmol) and a catalytic amount of 4-dimethylaminopyridine in dichloromethane (4 ml) at 0° C. After 1 h at 0° C., the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with dichloromethane and washed with hydrochloric acid 1N (10 ml), sodium hydroxide 2N (10 ml) and brine (10 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield N-cyclohexyl-N-methyl-2-nitrobenzamide (1.05 g, 74%) that was used in the next step without further purification.

後処理

  1. customat 0° C
  2. washwashed with hydrochloric acid 1N (10 ml), sodium hydroxide 2N (10 ml) and brine (10 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-59853f704ae5456e9200d87ca788263e
出典データセット
uspto-grants-2007_08
特許番号
US07253171B2

反応ノート

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