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

HRID 852233노트

반응식

HRID 852233 반응식
[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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 76688Cyclohexanemethylamine

생성물 1

HCID 799283N-cyclohexyl-N-methyl-2-nitrobenzamide수율 74.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59853f704ae5456e9200d87ca788263e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253171B2

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