Phenyl isocyanate → Pencycuron

HRID 1704751

Reaktionsgleichung

Reaktionsgleichung von HRID 1704751
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1>CCCCCC>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 7672Phenyl isocyanateHCID 8340834-chloro-N-cyclopentylbenzylamine

Produkt 1

HCID 91692PencycuronAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

A solution of 12 grams (0.1 mole) of phenylisocyanate in 50 ml of hexane was added dropwise to 21 grams (0.1 mole) of N-4-chlorobenzyl-N-cyclopentylamine in 400 ml of hexane under cooling and stirring conditions. After the addition, the temperature of the reaction mixture was gradually raised, and the solution was then stirred at 50° C. for about 7 hours. The mixture was cooled and filtered. The residue was recrystallized from a mixed solvent of hexane-ethyl alcohol. 31 grams of N-4-chlorobenzyl-N-cyclopentyl-N'-phenylurea were obtained. Yield: 95%. Melting point: 129°-134° C.

Aufarbeitung

  1. temperatureunder cooling
  2. additionAfter the addition
  3. temperaturethe temperature of the reaction mixture was gradually raised
  4. stirringthe solution was then stirred at 50° C. for about 7 hours
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. customThe residue was recrystallized from a mixed solvent of hexane-ethyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-3135366f812149b0991e7679a9603783
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04127673

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