Allyl chloride → N-allyl-N-formyl-2-methyl-4-nitroaniline

HRID 1029862Notes

Reaction equation

HRID 1029862 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH3:19])=[O:8].[CH2:20](Cl)[CH:21]=[CH2:22]>CN(C)C=O>[CH2:22]([N:9]([CH:7]=[O:8])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH3:19])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 11430Potassium CarbonateHCID 35570182-Methyl-4-nitrophenylformamide

Product 1

HCID 15724688N-allyl-N-formyl-2-methyl-4-nitroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

155 g of potassium carbonate were introduced into 500 ml of dimethylformamide. 50 g (0.28 mol) of N-formyl-2-methyl-4-nitroaniline were added to this mixture to give an orange solution, which became blood-red after 128.6 g (136.8 ml, 1.68 mol) of allyl chloride were added. The resultant reaction mixture was stirred overnight and subsequently poured into 1.5 1 of ice water. The crude product which deposited was extracted twice from the aqueous phase with 400 ml of dichloromethane in each case. The two combined dichloromethane phases were washed three times with 500 ml of water in each case, subsequently dried over sodium sulfate and then evaporated, to give 58.3 g of N-allyl-N-formyl-2-methyl-4-nitroaniline (yield: 95%) as an orange oil which crystallized in the refrigerator. The product had a melting point of 56° C. and the following physical/chemical properties:

Workup

  1. customto give an orange solution, which
  2. additionwere added
  3. customThe resultant reaction mixture
  4. extractionThe crude product which deposited was extracted twice from the aqueous phase with 400 ml of dichloromethane in each case
  5. washThe two combined dichloromethane phases were washed three times with 500 ml of water in each case
  6. dry with materialsubsequently dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-c9401284c2b3438ba0260d3441315445
Source dataset
uspto-grants-1992_04
Patent number
US05103060

Reaction notes

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