Diethylamine → 4-(4-chloro-2-nitrophenoxy)-N,N-diethylbenzamide

HRID 2197856Notes

Reaction equation

HRID 2197856 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.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>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:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 866154944-(4-Chloro-2-nitrophenoxy)benzoyl chloride

Product 1

HCID 511497004-(4-chloro-2-nitrophenoxy)-N,N-diethylbenzamide

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 diethylamine (469 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 (1.1 g, 100%).

Workup

  1. concentrationMixture was concentrated under vacuum

Sources & evidence

ORD record
ord-62b7b034acbe467c9c9f8fbcced311ab
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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