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

HRID 27996Notes

Reaction equation

HRID 27996 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[C:11]1([N:17]=[C:18]=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:26][C:27](N)=[O:28]>CO>[C:11]1([NH:17][C:18]([N:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:27]([NH:1][C:2]2[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=2)=[O:28])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1176UreaHCID 7672Phenyl isocyanateHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 233412451,3-Diphenyl-5-(3-Trichloromethyl-1,2,4-thiadiazol-5-yl)biuretYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
145 °C

Procedure

A glass pressure vessel was charged with 5.5 grams (0.03 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole, 7.4 grams (0.06 mole) phenyl 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 a urea by-product precipitates. The by-product was removed by filtration and the filtrate concentrated in vacuo to leave 9.0 grams of crude product. Trituration with cold methanol gave 2.8 grams (24% yield) of pure product; m.p. 170° 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
  7. customto leave 9.0 grams of crude product

Sources & evidence

ORD record
ord-b52e5629381a40c8b65e14aa7b9e230c
Source dataset
uspto-grants-1980_09
Patent number
US04224449

Reaction notes

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