N-Methylethylamine → 4-(4-chloro-2-nitrophenoxy)-N-ethyl-N-methylbenzamide

HRID 2197862Notes

Reaction equation

HRID 2197862 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][NH:22][CH2:23][CH3:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([N:22]([CH2:23][CH3:24])[CH3:21])=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 866154944-(4-Chloro-2-nitrophenoxy)benzoyl chloride

Product 1

HCID 684597124-(4-chloro-2-nitrophenoxy)-N-ethyl-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound from Example 126c (1.0 g, 3.2 mmol) in CH2Cl2 was added to a mixture of N-methylethanamine (379 mg, 6.41 mmol) in CH2Cl2. Mixture was stirred for 12 hours. Mixture was concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 50% EtOAc/hexane giving a yellow oil (1.03 g, 100%).

Workup

  1. concentrationMixture was concentrated under vacuum

Sources & evidence

ORD record
ord-e9fd660c7e894369a30b2a831f8a6184
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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