Chloroform → N-cyanomethyl trichloroacrylamide

HRID 2231847Notes

Reaction equation

HRID 2231847 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>CCCCCC>[C:11]([CH2:12][NH:13][C:3](=[O:4])[C:2]([Cl:1])=[C:6]([Cl:8])[Cl:7])#[N:10]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 131532,3,3-Trichloro-2-propenoyl chlorideHCID 11491918Aminoacetonitrile hydrochloride2×

Product 1

HCID 14349404N-cyanomethyl trichloroacrylamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A stirred mixture of 38.8 g (0.2 moles) trichloroacryloyl chloride, 18.5 g. (0.2 moles) aminoacetonitrile hydrochloride and.150 ml chloroform was refluxed for thirty hours, with evolution of gas and dissolution of most of the aminoacetonitrile hydrochloride. The mixture was filtered hot to remove unreacted aminoacetonitrile hydrochloride. The filtrate was stripped to give an oil. The oil was rubbed with hexane and soon solidified to give 36.1 g of the above-identified product as an off-white solid, which liquified at about 56°-59° C. A small portion of product was recrystallized from a benzene-hexane mixture to give a white solid, melting point 58°-60° C.

Workup

  1. filtrationThe mixture was filtered hot
  2. customto remove unreacted aminoacetonitrile hydrochloride
  3. customto give an oil

Sources & evidence

ORD record
ord-aa8adefaebbc46e3b957c9f7c97673b8
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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