Phosgene → 5-Methylsulfonylthiazol-2-yl isocyanate

HRID 1111593Notes

Reaction equation

HRID 1111593 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[S:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][N:10]=1>C(OCC)(=O)C>[CH3:14][S:11]([C:8]1[S:7][C:6]([N:5]=[C:1]=[O:2])=[N:10][CH:9]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 149317892-Amino-5-methylsulfonylthiazole

Product 1

HCID 540560325-Methylsulfonylthiazol-2-yl isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A saturated solution of phosgene in ethyl acetate (200 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Amino-5-methylsulfonylthiazole (0.1 mole) is added with stirring. After the addition is completed, the reaction mixture is heated at reflux for a period of about one hour. After this time the mixture is cooled, and the solid product formed is recovered by filtration. The solid is then dried to yield the desired product 5-methylsulfonylthiazol-2-yl isocyanate dimer.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperaturethe reaction mixture is heated
  5. temperatureat reflux for a period of about one hour
  6. temperatureAfter this time the mixture is cooled
  7. customthe solid product formed
  8. filtrationis recovered by filtration
  9. customThe solid is then dried

Sources & evidence

ORD record
ord-b3f20f36f27a497e9ca2dd554179e473
Source dataset
uspto-grants-1978_10
Patent number
US04118390

Reaction notes

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