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

HRID 2083598Notes

Reaction equation

HRID 2083598 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][S:6]([C:8]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1)=[O:7].[C:14](OCC)(=[O:16])C>>[CH3:5][S:6]([C:8]1[S:12][C:11]([N:13]=[C:1]=[O:2])=[N:10][N:9]=1)=[O:7].[CH3:5][S:6]([C:8]1[S:12][C:11]([N:13]=[C:14]=[O:16])=[N:10][N:9]=1)(=[O:2])=[O:7]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8857Ethyl Acetate2×HCID 203927285-(Methanesulfinyl)-1,3,4-thiadiazol-2-amine

Product 2

HCID 540842185-Methylsulfinyl-1,3,4-thiadiazol-2-yl isocyanateHCID 542537365-Methylsulfonyl-1,3,4-thiadiazol-2-yl isocyanate

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-methylsulfinyl-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-methylsulfonyl-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-26a87b02907e4fc9ac47c2e7050d3234
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

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