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]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.
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