Phosgene → HCID 54545133, compound

HRID 2287035Notes

Reaction equation

HRID 2287035 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[O:9][CH:10]([C:12]1[S:16][C:15]([NH2:17])=[N:14][N:13]=1)[CH3:11]>C(OCC)(=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[O:9][CH:10]([C:12]1[S:16][C:15]([N:17]=[C:1]=[O:2])=[N:14][N:13]=1)[CH3:11]

Participants

4

Reactant 2

HCID 6371Phosgene3×HCID 23460870HCID 23460870, compound

Product 1

HCID 54545133HCID 54545133, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

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 rotameter was charged with 50 milliliters of ethyl acetate saturated with phosgene at 20° C. (approximately 0.5 mole of phosgene). An additional 50 milliliters of ethylacetate was added, and 7.9 grams of 5-[1-(3,5-dichorophenoxy)ethyl]-2-amino-1,3,4-thiadiazole, (prepared above) in 30 milliliters of ethyl acetate was added. The resulting solution was stirred for 64 hours, and then purged with nitrogen until no COCl2 was detected. The solution was filtered and then topped at 70° C. in a roto-vac to form 10.0 grams of a viscous yellow oil of 5-[1-(3,5-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customA 500 milliliter, 3-neck flask equipped with a magnetic stirrer
  2. additionwas added
  3. custompurged with nitrogen until no COCl2
  4. filtrationThe solution was filtered
  5. customtopped at 70° C. in a roto-vac

Sources & evidence

ORD record
ord-ea7e67af10f84700b65126bd94a4f45e
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

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