Pyridine → N-(2-Bromoethyl)-p-nitrobenzamide

HRID 1085258

Reaction equation

HRID 1085258 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br.[NH2:14][CH2:15][CH2:16][Br:17].N1C=CC=CC=1>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:14][CH2:15][CH2:16][Br:17])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 458985N-(2-Bromoethyl)-p-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 30 ml of chloroform were added 3 g of 4-nitrobenzoyl chloride, 3.3 g of 2-aminoethyl bromide hydrobromide and 3.9 ml of pyridine under ice cooling, and they were stirred at the same temperature for 1 hour. The reaction mixture was then washed with water, and the resulting organic layer was concentrated to obtain a crude product of 2-(4-nitrobenzoylamino)ethyl bromide. Afterward, the latter was recrystallized from hexane/ethanol, the resulting crystals were collected by filtration, washed and dried to prepare 2.9 g of 2-(4-nitrobenzoylamino)ethyl bromide (compound 46).

Workup

  1. washThe reaction mixture was then washed with water
  2. concentrationthe resulting organic layer was concentrated

Sources & evidence

ORD record
ord-6552b384b67f4658950798dd857919fd
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Linked notes

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