Dimethylcarbamoyl Chloride → 1-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3,3-dimethylurea

HRID 899128Notes

Reaction equation

HRID 899128 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>ClCCl.O>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[C:25]([N:24]([CH3:28])[CH3:23])=[O:26])=[CH:15][CH:14]=1)#[N:13]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 690686254-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

Product 1

HCID 690725741-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3,3-dimethylureaYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile (5 g, 0.0242 mol; see Preparation C, step (ii) above) was taken in dry dichloromethane (50 mL) and cooled to 0° C. Triethylamine (4 mL, 0.03 mol), followed by N,N-dimethylcarbamoyl chloride (3.9 g, 0.03 mol), was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Purification by column chromatography using dichloromethane in methanol yielded 6 g of the sub-title compound as pale yellow liquid.

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-fa403931ca324fb4b549ad25703d6412
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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