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

HRID 867054Notes

Reaction equation

HRID 867054 reaction equation
[O:1]([C:8]([N:10]=[C:11]=[O:12])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([O:22][CH3:23])[C:17]([O:20][CH3:21])=[CH:18][CH:19]=1>O1CCOCC1>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([NH:13][C:11]([NH:10][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:9])=[O:12])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 227703,4-Dimethoxyaniline2×HCID 4148962Phenyl isocyanatoformate

Product 1

HCID 203173671-(3,4-Dimethoxyphenyl)-3-phenoxycarbonylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of phenoxycarbonylisocyanate (7.0 g., 0.043 mole) in 50 ml. of dioxane is added 4-aminoveratrole (6.57 g., 0.043 mole) under a nitrogen atmosphere while maintaining a temperature of 20°-25°. Following the addition of the 4-aminoveratrole, a second 50 ml. portion of dioxane is added and the solution refluxed for a period of one hour. Concentration of the reaction mixture under reduced pressure provides an oily solid residue. Titration of this residual material with about 40 ml. of cold carbon tetrachloride followed by crystallization from acetonitrile provides analytically pure 1-(3,4-dimethoxyphenyl)-3-phenoxycarbonylurea, m.p. 139.5°-142°.

Workup

  1. temperaturewhile maintaining a temperature of 20°-25°
  2. temperaturethe solution refluxed for a period of one hour
  3. customConcentration of the reaction mixture under reduced pressure provides an oily solid residue
  4. customof cold carbon tetrachloride followed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-84ca08b4c288427f890306fe4b321d6f
Source dataset
uspto-grants-1978_07
Patent number
US04102885

Reaction notes

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