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

HRID 1580669Notes

Reaction equation

HRID 1580669 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 is 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 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-methylthio-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

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

Sources & evidence

ORD record
ord-536659bb7bdf42cd9340c89373845ce3
Source dataset
uspto-grants-1976_01
Patent number
US03933839

Reaction notes

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