Chloroform → 2,3-Dichloropropanoyl isocyanate

HRID 866774Notes

Reaction equation

HRID 866774 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 isocyanateYield 72%

Procedure

99 g (1.40 moles) of chlorine were passed into a solution of 100 g (1.41 moles) of acrylamide in 1,000 ml of chloroform while stirring at about 0° to 5° C. The mixture was then stirred for a further 3 hours at about 20° C, after which 270 g (2.13 moles) of oxalyl chloride was added dropwise, while continuing the stirring. The solution was then heated to the boil under reflux, until the evolution of gas had ceased. Fractional distillation of the reaction solution gave 172 g (72% theory) of 2,3-dichloro-propionyl isocyanate of boiling point 38 to 41° C/1.0 mm Hg. ##STR76##

Workup

  1. stirringThe mixture was then stirred for a further 3 hours at about 20° C
  2. temperatureThe solution was then heated to the boil
  3. temperatureunder reflux, until the evolution of gas
  4. distillationFractional distillation of the reaction solution

Sources & evidence

ORD record
ord-b3ce25167c8b4ae0836369995793202e
Source dataset
uspto-grants-1978_07
Patent number
US04101575

Reaction notes

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