Hydrogen Bromide → Daimuron

HRID 441327Notes

Reaction equation

HRID 441327 reaction equation
[C:1]1([NH:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][C:2]=1C.[N+](C1C=CC=CC=1)([O-])=O.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH2:24].Br>CCCCCC>[CH3:22][C:23]([NH:12][C:10]([NH:9][C:1]1[CH:2]=[CH:3][C:4]([CH3:7])=[CH:5][CH:6]=1)=[O:11])([CH3:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 7407Alpha-MethylstyreneHCID 7416NitrobenzeneHCID 8536382,4-Dimethylphenylurea

Product 1

HCID 39238Daimuron

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

12.4 parts of 2,4 -xylylurea was suspended in 50 parts of nitrobenzene, and 30 parts of α-methylstyrene was added. The mixture was stirred while introducing anhydrous hydrobromic acid portionwise. When the amount of the mixture increased by 10 parts, the introduction of the hydrobromic acid was stopped. The reaction was then performed at 40° C. for 5 hours. The resulting reaction mixture was allowed to stand overnight. Then, 30 parts of n-hexane was added, and the mixture was further allowed to stand overnight. The precipitated crystals were recrystallized from 60% methanol to afford 13.4 parts of N-(α,α-dimethylbenzyl)-N'-(p-tolyl)urea having a melting point of 203° C.

Workup

  1. additionwas added
  2. temperatureWhen the amount of the mixture increased by 10 parts
  3. customThe resulting reaction mixture
  4. waitto stand overnight
  5. waitto stand overnight
  6. customThe precipitated crystals were recrystallized from 60% methanol

Sources & evidence

ORD record
ord-0c60defb3d584087828461a5357f9105
Source dataset
uspto-grants-1977_08
Patent number
US04039577

Reaction notes

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