Phenyl isocyanate → Pencycuron

HRID 1704751

Reaction equation

HRID 1704751 reaction equation
[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

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 8340834-Chloro-N-cyclopentylbenzylamine

Product 1

HCID 91692PencycuronYield 95%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3135366f812149b0991e7679a9603783
Source dataset
uspto-grants-1978_11
Patent number
US04127673

Linked notes

Loading…