Phosgene → HCID 54072011, compound

HRID 2287038Notes

Reaction equation

HRID 2287038 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:9][CH:10]([C:12]1[S:16][C:15]([NH2:17])=[N:14][N:13]=1)[CH3:11]>C(OC(=O)C)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][C:20]=1[Cl:21])[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 12880030HCID 12880030, compound

Product 1

HCID 54072011HCID 54072011, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 500 milliliter, 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 saturated with phosgene at 20° C. (approximately 0.5 mole of phosgene). An additional 50 milliliters of ethylacetate was added and 8.0 grams of 5-[1-(3,4-dichlorophenoxy)ethyl]-2-amino-1,3,4-thiadiazole, (prepared above) was added. The resulting solution was stirred for 17 hours with formation of an emulsion, and then purged with nitrogen until no COCl2 was detected. The solution was filtered, and topped at 70° C. in a roto-vac to form 9.0 grams of a viscous yellow oil of 5-[1-(3,4-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customA 500 milliliter, 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-9e96395f28874098b2e8dd02f6b69980
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

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