Phosgene → 5-Methylsulfonylthiazol-2-yl isocyanate

HRID 839808Notes

Reaction equation

HRID 839808 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-7935e57cb13e41e4aea22a75f622de11
Source dataset
uspto-grants-1978_06
Patent number
US04097485

Reaction notes

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