Hydrochloric Acid → Daimuron

HRID 441329Notes

Reaction equation

HRID 441329 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].Cl.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH2:20])=[O:19])=[CH:13][CH:12]=1>C(#N)C>[CH3:3][C:2]([NH:20][C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)=[O:19])([CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 7407Alpha-MethylstyreneHCID 12148N-(4-Methylphenyl)urea

Product 1

HCID 39238Daimuron

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

30 ml. of α-methylstyrene was placed in a 200 ml. reactor, and while externally cooling with ice, anhydrous hydrochloric acid was introduced at 0 to 10° C. When the weight of the mixture increased by 1.8 g, the introduction of the hydrochloric acid was stopped. 11.3 g of p-tolylurea and 40 parts of acetonitrile were added, and with stirring, the mixture was heated. After heating it for 4 hours at 40 ± 2° C., the reaction mixture was maintained at 20° C. for 3 days. The precipitated crystals were collected, and recrystallized from 70% methanol to afford 13.5 g of N-(α,α-dimethylbenzyl)-N'-(p-tolyl)urea having a melting point of 203° C.

Workup

  1. additionwas introduced at 0 to 10° C
  2. temperatureWhen the weight of the mixture increased by 1.8 g
  3. temperaturethe mixture was heated
  4. temperatureAfter heating it for 4 hours at 40 ± 2° C.
  5. customThe precipitated crystals were collected
  6. customrecrystallized from 70% methanol

Sources & evidence

ORD record
ord-6faf64ba5818451b91159f865e65f2d8
Source dataset
uspto-grants-1977_08
Patent number
US04039577

Reaction notes

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