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

HRID 441328Notes

Reaction equation

HRID 441328 reaction equation
C1([NH:9][C:10]([NH2:12])=[O:11])C=CC(C)=CC=1C.C(#N)C.[C:16](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH3:17].[CH3:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH2:28]>CCCCCC>[CH3:17][C:16]([NH:9][C:10]([NH:12][C:27]([CH3:26])([CH3:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11])([CH3:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7407Alpha-MethylstyreneHCID 70281(1-Chloro-1-methylethyl)benzeneHCID 8536382,4-Dimethylphenylurea

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

12.4 parts of 2,4-xylylurea was suspended in 50 parts of acetonitrile, and 7.7 parts of cumyl chloride and 24 parts of α-methylstyrene were added. With stirring, they were reacted at 40° C. for 6 hours. After allowing the reaction mixture to stand for one day, 50 parts of n-hexane was added. The mixture was further allowed to stand overnight. The precipitated crystals were collected, and recrystallized from 60% methanol to afford 12.5 parts of N-(α,α-dimethylbenzyl)-N'-(2,4,urea (III: R=--C6H3 (CH3)2 --2,4) having a melting point of 163° C.

Workup

  1. additionwere added
  2. customthey were reacted at 40° C. for 6 hours
  3. waitto stand overnight
  4. customThe precipitated crystals were collected
  5. customrecrystallized from 60% methanol

Sources & evidence

ORD record
ord-8386376868c148f2ae2c3364dbc6faee
Source dataset
uspto-grants-1977_08
Patent number
US04039577

Reaction notes

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