Benzene → 1,3-Dimethyl-5-(3-Trichloromethyl-1,2,4-thiadiazol-5-yl)biuret

HRID 27995Notes

Reaction equation

HRID 27995 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[CH3:11][N:12]=[C:13]=[O:14].[NH2:15][C:16](N)=[O:17].[CH:19]1C=CC=CC=1>>[CH3:11][NH:12][C:13]([N:15]([CH3:19])[C:16]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:17])=[O:14]

Participants

5

Reactant 4

HCID 241BenzeneHCID 1176UreaHCID 12228Methyl IsocyanateHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 233412441,3-Dimethyl-5-(3-Trichloromethyl-1,2,4-thiadiazol-5-yl)biuretYield 65%

Conditions

Temperature
145 °C

Procedure

A glass pressure vessel was charged with 27.5 grams (0.13 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole, 17.9 grams (0.31 mole) methyl isocyanate, and 250 milliliters benzene. A magnetic stirring bar was added and the vessel sealed. The stirred reaction mixture was heated at 145° C. for 1.5 hours and then allowed to cool to room temperature where a urea by-product precipitates. The by-product was removed by filtration and the filtrate concentrated in vacuo to leave 27.2 grams (65% yield) of product. Recrystallization from methanol gave an analytically pure sample; m.p. 94° C.

Workup

  1. additionA magnetic stirring bar was added
  2. customthe vessel sealed
  3. customThe stirred reaction mixture
  4. customprecipitates
  5. customThe by-product was removed by filtration
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f015a097b8da43e99cb995089103c23a
Source dataset
uspto-grants-1980_09
Patent number
US04224449

Reaction notes

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