Phosgene → HCID 54349766, compound

HRID 1862946Notes

Reaction equation

HRID 1862946 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][CH2:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][N:8]=1>C(OCC)(=O)C>[Cl:5][CH2:6][C:7]1[S:11][C:10]([N:12]=[C:1]=[O:2])=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 150317065-(Chloromethyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 54349766HCID 54349766, compound

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-chloromethyl-2-amino-1,3,4-thiadiazole (10 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 desired product 5-chloromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer as a solid.

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 desired product 5-chloromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer as a solid

Sources & evidence

ORD record
ord-0f5c7daada1c41aca4fdf045d6314c25
Source dataset
uspto-grants-1979_09
Patent number
US04167407

Reaction notes

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