Alpha-Methylstyrene → Daimuron

HRID 441330Notes

Reaction equation

HRID 441330 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH2:10])=[O:9])=[CH:3][CH:2]=1.[C:12](Cl)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13].CC(C1C=CC=CC=1)=C>CC(CC(C)C)=O>[CH3:13][C:12]([NH:10][C:8]([NH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)=[O:9])([CH3:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 12148N-(4-Methylphenyl)ureaHCID 70281(1-Chloro-1-methylethyl)benzene

Product 1

HCID 39238Daimuron

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

11.25 parts of p-tolylurea, 7.72 parts of cumyl chloride and 23.64 g of α-methylstyrene were added to 80 parts of methylisobutyl ketone, and the reaction was performed at 60° C. for 5 hours. After the reaction, the solvent was evaporated off at reduced pressure. The residue was washed with n-hexane, and recrystallized from a mixture of water and methanol to afford 5.4 parts of N-(α,α-dimethylbenzyl)-N'-(p-tolyl)urea.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated off at reduced pressure
  3. washThe residue was washed with n-hexane
  4. customrecrystallized from a mixture of water and methanol

Sources & evidence

ORD record
ord-b5b573ac54f1405891b6650c42d1c4fb
Source dataset
uspto-grants-1977_08
Patent number
US04039577

Reaction notes

Loading…