Dimethylcarbamoyl Chloride → 1-[3-(4-Cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylurea

HRID 899134Notes

Reaction equation

HRID 899134 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl.O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH2:13][CH2:12][CH2:11][N:10]([CH2:9][CH2:8][OH:7])[C:3]([N:2]([CH3:6])[CH3:1])=[O:4])=[CH:15][CH:16]=1)#[N:19]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 690715794-[3-(2-Hydroxyethylamino)propyl]benzonitrile

Product 1

HCID 690676201-[3-(4-Cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylureaYield 101.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylcarbamoyl chloride (3.9 g, 0.0368 mol) was added to a mixture of 4-[3-(2-hydroxyethylamino)propyl]benzonitrile (5 g, 0.025 mol; see step (i) above) and triethylamine (3.7 g, 0.368 mol) in dichloromethane (100 mL) at 0° C. Stirring was then continued 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. Solvent evaporation under reduced pressure, followed by purification by column chromatography (using 4% methanol in dichloromethane) yielded 7 g of the sub-title compound as a pale yellow, gummy liquid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent evaporation under reduced pressure
  5. customfollowed by purification by column chromatography (using 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4740ed437ffa44a6be61577d8a64ec8e
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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