Dimethylamine → N,N-Dimethyl-4-nitrobenzylamine

HRID 1701470Notes

Reaction equation

HRID 1701470 reaction equation
[CH3:1][NH:2][CH3:3].[N+:4]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1)([O-:6])=[O:5]>C(O)C>[CH3:1][N:2]([CH2:11][C:10]1[CH:13]=[CH:14][C:7]([N+:4]([O-:6])=[O:5])=[CH:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 74824-Nitrobenzyl chloride

Product 1

HCID 278498N,N-Dimethyl-4-nitrobenzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3 l of ethanol was added 750 ml of a 40% aqueous solution of dimethylamine and 500 g. of p-nitrobenzyl chloride was added gradually thereto with stirring. After complete dissolution, the reaction was carried out at 40° C. for 10 hours. After the reaction mixture was concentrated by distilling off the ethanol, the residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated by distilling off the ethyl acetate. The residue thus obtained was distilled under reduced pressure to give a yellow liquid which was the desired product boiling at 102° to 104° C./2 mmHg.

Workup

  1. dissolutionAfter complete dissolution
  2. concentrationAfter the reaction mixture was concentrated
  3. distillationby distilling off the ethanol
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. distillationby distilling off the ethyl acetate
  8. customThe residue thus obtained
  9. distillationwas distilled under reduced pressure
  10. customto give a yellow liquid which

Sources & evidence

ORD record
ord-3b5c3d80b51543d192b2a9777ae06ee9
Source dataset
uspto-grants-1980_03
Patent number
US04193800

Reaction notes

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