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Phosgene → 5-Fluorothiazol-2-yl Isocyanate

HRID 1764460
Notes
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Reaction equation

HRID 1764460 reaction equation
[NH2:1][C:2]1[S:3][C:4]([F:7])=[CH:5][N:6]=1.[C:8](Cl)(Cl)=[O:9]>C(OCC)(=O)C>[F:7][C:4]1[S:3][C:2]([N:1]=[C:8]=[O:9])=[N:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 100803855-Fluoro-1,3-thiazol-2-amine

Product 1

HCID 542471925-Fluorothiazol-2-yl Isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-5c4dff44133245c5b121868f9aa2b048
Source dataset
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04116969

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes