Phenylurea → N,N'-bis(alpha,alpha-dimethylbenzyl)urea

HRID 441326

Reaction equation

HRID 441326 reaction equation
C1([NH:7][C:8]([NH2:10])=[O:9])C=CC=CC=1.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:13].[C:20](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21]>C(#N)C>[CH3:13][C:12]([NH:7][C:8]([NH:10][C:20]([CH3:22])([CH3:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:9])([CH3:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6145PhenylureaHCID 7407Alpha-MethylstyreneHCID 70281(1-Chloro-1-methylethyl)benzene

Product 1

HCID 21420658N,N'-bis(alpha,alpha-dimethylbenzyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

102 parts of phenylurea was suspended in 80 parts of acetonitrile, and 25.4 parts of an α-methylstyrene solution containing 30.5% of cumyl chloride was added. With stirring, they were reacted at 40° C. for 5 hours. After allowing the reaction product to stand for 2 days, the precipitated crystals were collected and recrystallized from hydrous alcohol to afford 7.6 parts of N-phenyl-N'-(α,α-dimethylbenzyl) urea (III: R=C6H5). The melting point of the crystals was 193 to 194° C.

Workup

  1. additionwas added
  2. customthey were reacted at 40° C. for 5 hours
  3. customthe precipitated crystals were collected
  4. customrecrystallized from hydrous alcohol

Sources & evidence

ORD record
ord-9869a3120a6e4446876f3fb826ceeea7
Source dataset
uspto-grants-1977_08
Patent number
US04039577

Linked notes

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