Phosgene → 5-(Chloromethyl)-3-oxo-1,2-oxazole-2(3H)-carbonyl chloride

HRID 1380066Notes

Reaction equation

HRID 1380066 reaction equation
[Cl:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([OH:8])[CH:4]=1.[C:9](Cl)([Cl:11])=[O:10]>C1C=CC=CC=1>[Cl:11][C:9]([N:6]1[C:5](=[O:8])[CH:4]=[C:3]([CH2:2][Cl:1])[O:7]1)=[O:10]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 178516070HCID 178516070, compound

Product 1

HCID 136294255-(Chloromethyl)-3-oxo-1,2-oxazole-2(3H)-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 673 mg of 5-chloromethyl-3-hydroxyisoxazole, 19 ml of benzene and about 1 ml of liquified phosgene was stirred at room temperature for 5 hours. At the end of this time, the excess phosgene and the solvent were distilled off, giving 900 mg (yield 100% of theory) of the title compound, in the form of a colourless oil having a refractive index, nD24 =1.5391.

Workup

  1. distillationAt the end of this time, the excess phosgene and the solvent were distilled off

Sources & evidence

ORD record
ord-0baddd47e94d4faab0751a753e17e203
Source dataset
uspto-grants-1986_04
Patent number
US04579860

Reaction notes

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