Ethylamine → N-ethyl-2-chloro-5-nitrobenzamide

HRID 2116546Notes

Reaction equation

HRID 2116546 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:14]([NH2:16])[CH3:15]>ClCCl>[CH2:14]([NH:16][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:15]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 117637Benzoyl chloride, 2-chloro-5-nitro-

Product 1

HCID 4380195N-ethyl-2-chloro-5-nitrobenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, 2-chloro-5-nitrobenzoyl chloride (10 g, 45.5 mmol) in anhydrous dichloromethane (250 mL) with Amberlyst A-21 ion-exchange resin (17 g) was treated with a 2M ThF solution of ethylamine (45 mL). The mixture was stirred at rt under nitrogen overnight. After filtration, the filtrate was concentrated to give N-ethyl-2-chloro-5-nitrobenzamide (9.0 g, 39 mmol, 86% yield) as a yellow solid.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1ae18eb0fe2547c69e53cb448e01d1dd
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

Loading…