Dimethyl Sulfoxide → 1-[3-(4-Cyanophenyl)propyl]-3,3-dimethyl-1-(2-oxoethyl)urea
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:22]([CH2:28][CH2:29][OH:30])[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][N:22]([CH2:28][CH:29]=[O:30])[C:23]([N:25]([CH3:26])[CH3:27])=[O:24])=[CH:17][CH:18]=1)#[N:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Oxalyl chloride (4.84 g, 0.038 mol) was added dropwise to a stirred solution of DMSO (5.9 g, 0.0763 mol) and dichloromethane (100 mL) at −78° C. After 15 min at the same temperature, 1-[3-(4-cyanophenyl)propyl]-1-(2-hydroxyethyl)-3,3-dimethylurea (7 g, 0.0254 mol) in dichloromethane was added and stirring continued for 3 h under a nitrogen atmosphere. Triethylamine (12.8 g, 0.127 mol) was added (dropwise), and the reaction mixture was then warmed slowly to −30° C. The reaction mixture was quenched with 10% citric acid (aq.) and extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to yield 6.5 g of the crude title compound, which was used without further purification.
Workup
- customThe reaction mixture was quenched with 10% citric acid (aq.)
- extractionextracted with dichloromethane
- washThe organic layer was washed with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-dab20cf7f05647a39865045bf4d4b07b
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07354917B2
Reaction notes
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