Phosgene → 5-Methoxy-1,3,4-thiadiazol-2-yl isocyanate

HRID 460794Notes

Reaction equation

HRID 460794 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][N:8]=1>C(OCC)(=O)C>[CH3:5][O:6][C:7]1[S:11][C:10]([N:12]=[C:1]=[O:2])=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 123887555-Methoxy-1,3,4-thiadiazol-2-amine

Product 1

HCID 451234665-Methoxy-1,3,4-thiadiazol-2-yl isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A saturated solution of phosgene in ethyl acetate (100 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-methoxy-2-amino-1,3,4-thiadiazole (40 grams) in ethyl acetate (300 ml) is added to the reaction vessel, and the resulting mixture is stirred for a period of about 16 hours, resulting in the formation of a precipitate. The reaction mixture is then purged with nitrogen gas to remove unreacted phosgene. The purged mixture is then filtered to recover the precipitate. The precipitate is then recrystallized to yield the desired product 5-methoxy-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customequipped with a mechanical stirrer
  2. customresulting in the formation of a precipitate
  3. customThe reaction mixture is then purged with nitrogen gas
  4. customto remove unreacted phosgene
  5. filtrationThe purged mixture is then filtered
  6. customto recover the precipitate
  7. customThe precipitate is then recrystallized

Sources & evidence

ORD record
ord-f5751b201d6945b6b9099c54fdb48384
Source dataset
uspto-grants-1977_12
Patent number
US04061648

Reaction notes

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