Phosgene → 5-Bromothiazol-2-yl Isocyanate

HRID 2083612Notes

Reaction equation

HRID 2083612 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[C:8](Cl)(Cl)=[O:9]>C(OCC)(=O)C>[Br:7][C:4]1[S:3][C:2]([N:1]=[C:8]=[O:9])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 436002-Thiazolamine, 5-bromo-

Product 1

HCID 230622645-Bromothiazol-2-yl Isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-bromothiazole (19.0 grams) and a saturated solution of phosgene in ethyl acetate (200 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux with stirring for a period of about 3 hours. After this time the reaction mixture was cooled and filtered to recover the desired product 5-bromothiazol-2-yl isocyanate dimer as a fine yellow powder.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. temperatureAfter this time the reaction mixture was cooled
  6. filtrationfiltered
  7. customto recover the desired product 5-bromothiazol-2-yl isocyanate dimer as a fine yellow powder

Sources & evidence

ORD record
ord-56355af5b2e741299394915cb23d9b7e
Source dataset
uspto-grants-1978_04
Patent number
US04086240

Reaction notes

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