Water → Urea, 1,1-diethyl-3-phenyl-

HRID 234491Notes

Reaction equation

HRID 234491 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([N:10]([CH2:14][CH3:15])[C:11](Cl)=[O:12])[CH3:9].O>N1C=CC=CC=1>[CH2:8]([N:10]([CH2:14][CH3:15])[C:11](=[O:12])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 6916Diethylcarbamoyl chloride

Product 1

HCID 13906Urea, 1,1-diethyl-3-phenyl-Yield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step.

Workup

  1. customto rise to RT
  2. extractionIt is extracted with AcOEt
  3. washwashed with water and with a 5% solution of potassium hydrogensulfate
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum
  6. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-a4ee839fe604418abe2940807a02bfe6
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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