2,3,3-Trichloro-2-propenoyl chloride → N-cyanomethyl trichloroacrylamide

HRID 1447984Notes

Reaction equation

HRID 1447984 reaction equation
[Cl:1][C:2](=[C:6]([Cl:8])[Cl:7])[C:3](Cl)=[O:4].Cl.[NH2:10][CH2:11][C:12]#[N:13]>C(Cl)(Cl)Cl>[C:11]([CH2:12][NH:13][C:3](=[O:4])[C:2]([Cl:1])=[C:6]([Cl:8])[Cl:7])#[N:10]

Participants

4

Reactant 2

HCID 131532,3,3-Trichloro-2-propenoyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 14349404N-cyanomethyl trichloroacrylamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A slurry of 38.8 g (0.2 mol) trichloroacrylyl chloride and 18.5 g (0.2 mol) aminoacetonitrile hydrochloride in 150 ml chloroform was stirred and heated under reflux for 30 hours, while gases evolved and most of the hydrochloride salt dissolved. The reaction mixture was filtered while hot and the solvent evaporated under reduced pressure to give 36.1 g of N-cyanomethyl trichloroacrylamide, as an off-white solid melting at 56°-59° C. Recrystallization from benzene-hexane gave a white solid melting at 58°-60° C. Elemental analysis for C5H3Cl3N2O showed: %Cl, calc. 49.8, found 50.0.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 hours, while gases
  3. dissolutiondissolved
  4. filtrationThe reaction mixture was filtered while hot and the solvent
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d4c44e90fb894741bf3e55581b9da4f9
Source dataset
uspto-grants-1979_12
Patent number
US04179441

Reaction notes

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