Phosgene → HCID 54118858, compound

HRID 596740Notes

Reaction equation

HRID 596740 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1([C:12]2[S:16][C:15]([NH2:17])=[N:14][N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C(OCC)(=O)C>[CH3:5][C:6]1([C:12]2[S:16][C:15]([N:17]=[C:1]=[O:2])=[N:14][N:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 1760374957235-61-7

Product 1

HCID 54118858HCID 54118858, 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-(1-methylcyclohexyl)-2-amino-1,3,4-thiadiazole (6 grams) in ethyl acetate (100 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 filtered to recover the desired product 5-(1-methylcyclohexyl)-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 filtered
  6. customto recover the desired product 5-(1-methylcyclohexyl)-1,3,4-thiadiazol-2-yl isocyanate dimer

Sources & evidence

ORD record
ord-2d99621a48924e04876ab6952201a5ae
Source dataset
uspto-grants-1977_03
Patent number
US04012223

Reaction notes

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