Phosgene → HCID 13021505, compound

HRID 2287230Notes

Reaction equation

HRID 2287230 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl: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>[Cl: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 3155973HCID 3155973, compound

Product 1

HCID 13021505HCID 13021505, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 300 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 ethyl acetate saturated with phosgene at 20° C. (approximately 0.5 mole of phosgene). An additional 100 milliliters of ethylacetate was added; 9.8 grams of 5-[1-(2-chlorophenoxy)ethyl]-2-amino-1,3,4-thiadiazole (prepared above) at a temperature from 0° C. to room temperature was added. The resulting solution was stirred for 17 hours with formation of an emulsion and then the flask was purged with nitrogen until no COCl2 was detected. The solution was filtered, and topped at 70° C. on a roto-vac to form 9.9 grams of a gooey yellow oil of 5-[1-(2-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customA 300 milliliter, 3-neck flask equipped with a magnetic stirrer
  2. customthe flask was purged with nitrogen until no COCl2
  3. filtrationThe solution was filtered
  4. customtopped at 70° C. on a roto-vac

Sources & evidence

ORD record
ord-2bc0759a4a224fdfbebc833e289c6cfe
Source dataset
uspto-grants-1981_05
Patent number
US04269983

Reaction notes

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