Urea → 1-Benzoyl-3-methyl-5-(3-trichloromethyl-1,2,4-thiadiazol-5-yl)biuret

HRID 27997

Reaction equation

HRID 27997 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([C:11]([Cl:14])([Cl:13])[Cl:12])[N:7]=1)=[O:4].[C:15]([N:23]=[C:24]=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.NC(N)=O>C1C=CC=CC=1>[C:15]([NH:23][C:24]([N:2]([CH3:1])[C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([C:11]([Cl:12])([Cl:14])[Cl:13])[N:7]=1)=[O:4])=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 78210Benzoyl isocyanateHCID 233412461-Methyl-3-(3-trichloromethyl-1,2,4-thiadiazol-5-yl)urea

Product 1

HCID 233412431-Benzoyl-3-methyl-5-(3-trichloromethyl-1,2,4-thiadiazol-5-yl)biuretYield 35.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
145 °C

Procedure

A glass pressure vessel was charged with 5.5 grams (0.02 mole) 1-methyl-3-(3-trichloromethyl-1,2,4-thiadiazol-5-yl)urea, 3.2 grams (0.02 mole) benzoyl isocyanate and 50 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 4.5 grams of starting urea precipitates. The urea was removed by filtration and the filtrate concentrated in vacuo to leave 3.0 grams of residue. Extraction of the residue with hot cyclohexane, followed by cooling the extract yielded 0.2 grams (11% selectivity) of pure product; m.p. 70° C.

Workup

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

Sources & evidence

ORD record
ord-8612e1f7ac334909a950534ef2d2bb70
Source dataset
uspto-grants-1980_09
Patent number
US04224449

Linked notes

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