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

HRID 972146Notes

Reaction equation

HRID 972146 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][S:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][N:8]=1>C(OCC)(=O)C>[CH3:5][S: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 213905-(Methylsulfanyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 537505795-Methylthio-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-methylthio-2-amino-1,3,4-thiadiazole (45 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 preciptate. The reaction mixture is then purged with nitrogen gas to to remove unreacted phosgene. The purged mixture is filtered to recover the precipitate. The precipitate is then recrystallized to yield the desired product 5-methylthio-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

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

Sources & evidence

ORD record
ord-620609275dd54ff6977dff1da09d750c
Source dataset
uspto-grants-1977_10
Patent number
US04052191

Reaction notes

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