Triethylamine → N-Cyclohexyl-N-methyl-2-nitrobenzamide

HRID 852233Notes

Reaction equation

HRID 852233 reaction equation
[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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 76688Cyclohexanemethylamine

Product 1

HCID 799283N-Cyclohexyl-N-methyl-2-nitrobenzamideYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-59853f704ae5456e9200d87ca788263e
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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