Dimethyl Sulfoxide → 1-[2-(4-Cyanophenoxy)ethyl]-3,3-dimethyl-1-(2-oxoethyl)urea

HRID 899129Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:13]1[CH:30]=[CH:29][C:16]([O:17][CH2:18][CH2:19][N:20]([CH2:26][CH2:27][OH:28])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][N:20]([CH2:26][CH:27]=[O:28])[C:21]([N:23]([CH3:24])[CH3:25])=[O:22])=[CH:29][CH:30]=1)#[N:12]

Participants

Conditions

Temperature: -30 °C

Procedure

Oxalyl chloride (6.3 g, 0.0497 mol) was added dropwise to a stirred solution of DMSO (7.6 g, 0.094 mol) and dichloromethane (100 mL) at −78° C. After stirring for 15 min at the same temperature, 1-[2-(4-cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3,3-dimethylurea (6 g, 0.0325 mol; see step (i) above) in dichloromethane was added and stirring continued for 3 h under a nitrogen atmosphere. Triethylamine (16.4 mL, 0.1625 mol) was added dropwise and the reaction mixture was then warmed slowly to −30° C. The reaction mixture was quenched with an aqueous solution of citric acid, and the resulting mixture extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure yielded 4.5 g of the crude title compound, which was used without further purification.

Workup

additionwas added
customThe reaction mixture was quenched with an aqueous solution of citric acid
extractionthe resulting mixture extracted with dichloromethane
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
customSolvent evaporation under reduced pressure

Sources & evidence

ORD record: ord-70a4fcf17f134367a832cf86d04febfa
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354917B2

Reaction notes

Loading…