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

HRID 435906Notes

Reaction equation

HRID 435906 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][S:6]([C:9]1[S:13][C:12]([NH2:14])=[N:11][N:10]=1)(=[O:8])=[O:7]>C(OCC)(=O)C>[CH3:5][S:6]([C:9]1[S:13][C:12]([N:14]=[C:1]=[O:2])=[N:11][N:10]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 164543745-(Methanesulfonyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 542537365-Methylsulfonyl-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-methylsulfonyl-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 mixure 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 mixure is then filtered
  6. customto recover the precipitate
  7. customThe precipitate is then recrystallized

Sources & evidence

ORD record
ord-7553b878a1b64f37b525b20534e36f0e
Source dataset
uspto-grants-1977_02
Patent number
US04007031

Reaction notes

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