3,4-Dimethoxyaniline → 1-(3,4-Dimethoxyphenyl)-3-methoxycarbonylurea

HRID 867055Notes

Reaction equation

HRID 867055 reaction equation
[CH3:1][O:2][C:3]([N:5]=[C:6]=[O:7])=[O:4].[NH2:8][C:9]1[CH:10]=[C:11]([O:17][CH3:18])[C:12]([O:15][CH3:16])=[CH:13][CH:14]=1>O1CCOCC1>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])=[O:7])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 4156749Methyl isocyanatoformate

Product 1

HCID 203173501-(3,4-Dimethoxyphenyl)-3-methoxycarbonylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of methoxycarbonylisocyanate (3.78 g. 0.0374 mole) in 45 ml. of dioxane is added 4-aminoveratrole (5.73 g., 0.037 mole) while maintaining a temperature of 20°-30°. After completing the addition, another 45 ml. portion of dioxane is added and the mixture then heated at reflux for a period of one hour. Evaporation of the solvent and crystallization of residual material from nitromethane provides analytically pure 1-(3,4-dimethoxyphenyl)-3-methoxycarbonylurea, m.p. 168°-170°.

Workup

  1. temperaturewhile maintaining a temperature of 20°-30°
  2. additionthe addition
  3. temperaturethe mixture then heated
  4. temperatureat reflux for a period of one hour
  5. customEvaporation of the solvent and crystallization of residual material from nitromethane

Sources & evidence

ORD record
ord-6d870d23daf34fb9aca2697e34f26a28
Source dataset
uspto-grants-1978_07
Patent number
US04102885

Reaction notes

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