Phosgene → HCID 12799748, compound

HRID 1446952Notes

Reaction equation

HRID 1446952 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][S:6][C:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][N:11]=1)([CH3:9])[CH3:8]>C(OC(=O)C)C>[CH3:5][S:6][C:7]([C:10]1[S:14][C:13]([N:15]=[C:1]=[O:2])=[N:12][N:11]=1)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 12799747HCID 12799747, compound

Product 1

HCID 12799748HCID 12799748, 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 and then with 20 grams of phosgene. An additional 50 milliliters of ethylacetate and 6.6 grams (0.035 mole) of 5-(1-methylthio-1-methylethyl)-2-amino-1,3,4-thiadiazole (prepared above) at a temperature of 0° C. was added. The resulting mixture was stirred for 17 hours at room temperature and then the flask was purged with nitrogen until no COCl2 was detected. The slurry was filtered, and the filter cake was dried in a vacuum oven to a m.p. of 161°-164° C., and the filtrate was topped on a roto-vac to yield more crystals with a m.p. of 161°-162° C., which were combined with the first crystals to yield 7.1 grams of 5-(1-methylthio-1-methylethyl)-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 slurry was filtered
  4. customthe filter cake was dried in a vacuum oven to a m.p. of 161°-164° C.
  5. customto yield more crystals with a m.p. of 161°-162° C., which

Sources & evidence

ORD record
ord-306f79adf99143478035fe645744403b
Source dataset
uspto-grants-1982_02
Patent number
US04314842

Reaction notes

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