Phosgene → 5-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate

HRID 444369Notes

Reaction equation

HRID 444369 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl: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>[Cl: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 31559725-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-amine

Product 1

HCID 130207645-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 500 millileter, 3-neck flask equipped with a magnetic stirrer, thermometer, dry ice condensor/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). Additional 100 ml. of ethylacetate was added; (8.9 grams of 5-[1-(4-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 through a Whatman #42 filter paper to yield a slightly cloudy solution which was topped at 60 degrees centigrade with a roto-vac to form 9.2 grams of a pale yellow goop of 5-[1-(4-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customA 500 millileter, 3-neck flask equipped with a magnetic stirrer
  2. additionwas added
  3. customthe flask was purged with nitrogen until no COCl2
  4. filtrationThe solution was filtered through a Whatman #42
  5. filtrationfilter paper
  6. customto yield a slightly cloudy solution which
  7. customwas topped at 60 degrees centigrade with a roto-vac

Sources & evidence

ORD record
ord-d5ce8d4525664a9aa45bb750c5a26806
Source dataset
uspto-grants-1981_04
Patent number
US04264353

Reaction notes

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