Phosgene → HCID 53680789, compound

HRID 1856100Notes

Reaction equation

HRID 1856100 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH:11]([C:13]2[S:17][C:16]([NH2:18])=[N:15][N:14]=2)[CH3:12])=[CH:8][CH:7]=1>C(OC(=O)C)C>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH:11]([C:13]2[S:17][C:16]([N:18]=[C:1]=[O:2])=[N:15][N:14]=2)[CH3:12])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6371Phosgene3×HCID 17604534HCID 17604534, compound

Product 1

HCID 53680789HCID 53680789, 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 4.8 grams of 5-[1-(4-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole (prepared above) was added, 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 4.0 grams of a viscous orange oil of 5-[1-(4-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. filtrationfiltered
  4. customto remove a small amount of insoluble sediment
  5. customwas topped on a roto-vac at 70° C.

Sources & evidence

ORD record
ord-9e0ce0890df742ec99babcd31ead9d8d
Source dataset
uspto-grants-1980_08
Patent number
US04218236

Reaction notes

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