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

HRID 436231Notes

Reaction equation

HRID 436231 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([C:8]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1)[CH:6]=[CH2:7]>C(OCC)(=O)C>[CH2:5]([C:8]1[S:12][C:11]([N:13]=[C:1]=[O:2])=[N:10][N:9]=1)[CH:6]=[CH2:7]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 203926755-Allyl-2-amino-1,3,4-thiadiazole

Product 1

HCID 538389725-Allyl-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-allyl-2-amino-1,3,4-thiadiazole (50 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-allyl-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-f853ebf73d5c4252b82439f70901f1ac
Source dataset
uspto-grants-1977_02
Patent number
US04008068

Reaction notes

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