Dimethylformamide → N-Cyano-N-vinylbenzylacetamide

HRID 64944Notes

Reaction equation

HRID 64944 reaction equation
[Na].[C:2]([NH:5][C:6]#[N:7])(=O)[CH3:3].[CH:8]([CH:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:9].CN(C)C=[O:21]>>[C:6]([N:5]([CH:2]=[CH2:3])[C:9](=[O:21])[CH2:8][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)#[N:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 151267N-AcetylcyanamideHCID 5360545SodiumHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 57204927N-Cyano-N-vinylbenzylacetamide

Procedure

23.3 g (0.2 mol +10% excess) of the sodium salt of acetylcyanamide and 30.5 g (0.2 mol) of vinylbenzyl chloride (technical mixture of isomers containing approx. 40% of the para-component and 60% of the meta-component) are reacted in 100 ml of dimethylformamide for 8 hours at 48°-50° C., when the reaction is complete the mixture is filtered with suction, the filtrate is introduced into 300 g of ice and 500 ml of water while stirring vigorously and the mixture is then extracted with ethyl acetate. The ethyl acetate solution is dried with anhydrous sodium sulfate and filtered with suction, the filtrate is decolourised with active charcoal, the solution is filtered and the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator. The residue is dried to constant weight at 40° C./0.13 mbar. This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar.

Workup

  1. additioncontaining approx. 40% of the para-component and 60% of the meta-component)
  2. filtrationis filtered with suction
  3. additionthe filtrate is introduced into 300 g of ice and 500 ml of water
  4. extractionthe mixture is then extracted with ethyl acetate
  5. dry with materialThe ethyl acetate solution is dried with anhydrous sodium sulfate
  6. filtrationfiltered with suction
  7. filtrationthe solution is filtered
  8. concentrationthe filtrate is concentrated in vacuo at 40° C. on a rotary evaporator
  9. customThe residue is dried to constant weight at 40° C./0.13 mbar
  10. customThis gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube
  11. distillationdistillation at 130°-145° C./0.7 mbar

Sources & evidence

ORD record
ord-961aef875ae7459ea50882cc136e09e1
Source dataset
uspto-grants-1986_09
Patent number
US04611041

Reaction notes

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