Phosgene → HCID 54476191, compound

HRID 1856097Notes

Reaction equation

HRID 1856097 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[O:8][CH:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][N:12]=1)[CH3:10]>C(OC(=O)C)C>[CH3:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[O:8][CH:9]([C:11]1[S:15][C:14]([N:16]=[C:1]=[O:2])=[N:13][N:12]=1)[CH3:10]

Participants

4

Reactant 2

HCID 6371Phosgene3×HCID 17604532HCID 17604532, compound

Product 1

HCID 54476191HCID 54476191, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 500 milliliter, 3-neck flask equipped with a magnetic stirrer, thermometer, dry ice condenser/drying tube and inlet from a phosgene (COCl2) tank via a calibrated rotometer was charged with 50 milliliters of ethylacetate which was saturated with phosgene at 20° C. (approximately 0.5 mole of phosgene) and cooled in an ice bath. An additional 50 milliliters of ethylacetate was added and then 6.8 grams of 5-[1-(2-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole, (prepared above); a cloudy solution formed, the solution was stirred overnight, and then filtered to remove a small amount of insoluble sediment. The clear solution was topped on a roto-vac at 70° C. to form 8.1 grams of a viscous yellow residue of 5-[1-(2-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customA 500 milliliter, 3-neck flask equipped with a magnetic stirrer
  2. temperaturecooled in an ice bath
  3. customa cloudy solution formed
  4. filtrationfiltered
  5. customto remove a small amount of insoluble sediment
  6. customwas topped on a roto-vac at 70° C.

Sources & evidence

ORD record
ord-a8fce6c4426348afbac695f0160a2e72
Source dataset
uspto-grants-1980_08
Patent number
US04218236

Reaction notes

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