Phosgene → 2-Isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 1287178Notes

Reaction equation

HRID 1287178 reaction equation
[C:1](Cl)(Cl)=[O:2].[F:5][C:6]([F:14])([F:13])[C:7]1[S:8][C:9]([NH2:12])=[N:10][N:11]=1>C(OCC)(=O)C>[F:5][C:6]([F:14])([F:13])[C:7]1[S:8][C:9]([N:12]=[C:1]=[O:2])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 826341,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-

Product 1

HCID 131418952-Isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A saturated solution of phosgene in ethyl acetate (100 ml) was charged into a glass reaction flask equipped with a mechanical stirrer. A slurry of 2-trifluoromethyl-5-amino-1,3,4-thiadiazole (10 grams) in ethyl acetate (300 ml) was added to the reaction vessel and the resulting mixture was stirred for a period of about 16 hours resulting in the formation of a precipitate. The reaction mixture was then purged with nitrogen gas to remove unreacted phosgene. The purged mixture was then filtered to recover the desired product 2-trifluoromethyl-1,3,4-thiadiazol-5-yl isocyanate dimer.

Workup

  1. customequipped with a mechanical stirrer
  2. customresulting in the formation of a precipitate
  3. customThe reaction mixture was then purged with nitrogen gas
  4. customto remove unreacted phosgene
  5. filtrationThe purged mixture was then filtered
  6. customto recover the desired product 2-trifluoromethyl-1,3,4-thiadiazol-5-yl isocyanate dimer

Sources & evidence

ORD record
ord-a10e7c7066dc4c058e7dd2fefdcbf227
Source dataset
uspto-grants-1976_10
Patent number
US03984228

Reaction notes

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