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Phosgene → 5-Fluorothiazol-2-yl Isocyanate

HRID 839804
Notes
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Reaction equation

HRID 839804 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-c53a22655a0f4c719a1c0c47911bdacc
Source dataset
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04097485

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes