Chloroform → 2,3-Dichloropropanoyl isocyanate

HRID 259170Notes

Reaction equation

HRID 259170 reaction equation
ClCl.[C:3]([NH2:7])(=[O:6])C=C.[C:8]([Cl:13])(=O)[C:9](Cl)=[O:10].[CH:14]([Cl:17])(Cl)Cl>>[Cl:13][CH:8]([CH2:14][Cl:17])[C:9]([N:7]=[C:3]=[O:6])=[O:10]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6579AcrylamideHCID 24526ChlorineHCID 65578Oxalyl chloride

Product 1

HCID 203185352,3-Dichloropropanoyl isocyanate

Conditions

Temperature
20 °C

Procedure

99 g (1.40 mol) of chlorine are introduced with stirring at about 0 to 5° C. into a solution of 100 g of acrylic acid amide in 1000 ml of chloroform. After stirring for 3 hours at about 20° C., 270 g (2.13 mol) of oxalyl chloride are added dropwise with continued stirring. The solution is then boiled under reflux until the evolution of gas is complete. Fractional distillation of the reaction solution gives 172 g (72 % of the theoretical amount) of 2,3-dichloropropionyl isocyanate boiling at 38 to 41° C./1.0 Torr.

Workup

  1. temperatureunder reflux until the evolution of gas
  2. distillationFractional distillation of the reaction solution

Sources & evidence

ORD record
ord-1b2027bcf7c744eca3cc26229f213ca9
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

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