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

HRID 27997

Reaktionsgleichung

Reaktionsgleichung von HRID 27997
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 233412431-Benzoyl-3-methyl-5-(3-trichloromethyl-1,2,4-thiadiazol-5-yl)biuretAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8612e1f7ac334909a950534ef2d2bb70
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224449

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