Dimethylcarbamoyl Chloride → 1,1-DIME-3-(3-HYDROXYPHENYL)UREA

HRID 2164864Notes

Reaction equation

HRID 2164864 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]([CH3:14])[C:11](Cl)=[O:12]>O1CCCC1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:11]([N:10]([CH3:14])[CH3:9])=[O:12])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 115683-Aminophenol

Product 1

HCID 785621,1-DIME-3-(3-HYDROXYPHENYL)UREA

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

m-Aminophenol (10 g) and N,N-dimethylcarbamoyl chloride (7.42 g) are dissolved in tetrahydrofuran (65 ml) and the solution is stirred at 30° C. for 4 hours. The solvent is evaporated under reduced pressure and the solid residue is suspended in water. The mixture is filtered, washed well with water, and dried in a desiccator to give N-(3-hydroxyphenyl)-N',N'-dimethylurea which melts at 198° C. (decomp.) as measured on a Kofler bench. (U.S. Pat. No. 3,488,376 reports m.pt. 194°-197° C.).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. filtrationThe mixture is filtered
  3. washwashed well with water
  4. customdried in a desiccator

Sources & evidence

ORD record
ord-dc048b3e57684740aecf6779f451a7b8
Source dataset
uspto-grants-1985_03
Patent number
US04507445

Reaction notes

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