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

HRID 1531998Notes

Reaction equation

HRID 1531998 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].C1COCC1.[CH2:19]([NH2:21])[CH3:20]>ClCCl>[CH2:19]([NH:21][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])[CH3:20]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 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-12290228db9b454f9902bdcf803eb53f
Source dataset
uspto-grants-2001_03
Patent number
US06200995B1

Reaction notes

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