Phosgene → 5-Bromothiazol-2-yl Isocyanate

HRID 1764456Notes

Reaction equation

HRID 1764456 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-b6b0d855c2b04189993fdd26583273ea
Source dataset
uspto-grants-1978_09
Patent number
US04116969

Reaction notes

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