Dimethylformamide → 2-(Chloromethyl)-1-methyl-4-nitrobenzene

HRID 1075326Notes

Reaction equation

HRID 1075326 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[CH2:4]NC(=O)C.P(Cl)(Cl)([Cl:18])=O.CN(C)C=O>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[CH2:4][Cl:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 13115425HCID 13115425, compound

Product 1

HCID 1879522-(Chloromethyl)-1-methyl-4-nitrobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of N-(2-methyl-5-nitrobenzyl)acetamide (3.12 g; 0.015 mol), phosphorus oxychloride (5.12 g; 0.032 mol) and dimethylformamide (2.19 g; 0.03 mol) in xylene (50 ml) is refluxed for one hour. The reaction mixture is then washed with water and the solvent evaporated. This treatment produces 2.36 g (i.e., 85% yield) of product having a melting point of 56° to 62° C.

Workup

  1. washThe reaction mixture is then washed with water
  2. customthe solvent evaporated
  3. customThis treatment produces 2.36 g (i.e., 85% yield) of product

Sources & evidence

ORD record
ord-c16194a0f528498b88877b1dd3a9842e
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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