1,1-Dichloroethane → 3-Chloro-2-methylpropanoyl isocyanate

HRID 1650927Notes

Reaction equation

HRID 1650927 reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(Cl)(=O)[C:8](Cl)=[O:9].[Cl:13]C(Cl)C>Cl>[CH3:3][CH:2]([CH2:4][Cl:13])[C:1]([N:6]=[C:8]=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6595MethacrylamideHCID 65578Oxalyl chloride

Product 1

HCID 137662253-Chloro-2-methylpropanoyl isocyanate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

Into a suspension of methacrylamide (106 g; 1.25 mol) in dichloroethane (600 ml), dry hydrogen chloride gas was blown while cooling with ice for about 1 hour. Then, oxalyl chloride (243.9 g; 1.92 mol) was dropwise added thereto while continuing hydrogen chloride blowing and ice cooling. The resultant mixture was heated to reflux, and the refluxing was continued for 30 minutes. After being allowed to cool, the reaction mixture was distilled under reduced pressure to give alpha-methyl-beta-chloropropionyl isocyanate.

Workup

  1. temperaturewhile cooling with ice for about 1 hour
  2. temperatureto reflux
  3. temperatureto cool
  4. distillationthe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-1d1aaef925914350a8c885d0d6004d21
Source dataset
uspto-grants-1990_05
Patent number
US04925982

Reaction notes

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