Phosgene → 5-Methylbenzothiazol-2-yl isocyanate

HRID 973152Notes

Reaction equation

HRID 973152 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:9]=2[N:10]=1>C(OCC)(=O)C>[CH3:15][C:12]1[CH:13]=[CH:14][C:8]2[S:7][C:6]([N:5]=[C:1]=[O:2])=[N:10][C:9]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 26889Benzothiazole, 2-amino-5-methyl-

Product 1

HCID 450774585-Methylbenzothiazol-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-methylbenzothiazole (0.1 mole) is added with stirring. After the addition is completed, the reaction mixture is heated at reflux for a period of about 1 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-methylbenzothiazol-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 1 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-990aadeb5eb0479da99e98c6d28f1738
Source dataset
uspto-grants-1977_10
Patent number
US04055569

Reaction notes

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