[OH:1][N:2]=[C:3]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]([CH2:23][CH:24]=[CH:25][CH3:26])[CH2:17][C:18](OCC)=[O:19])=[O:15])=[CH:9][CH:8]=1)[CH2:4][CH2:5][CH3:6].O(C)[Na]>CO>[CH2:23]([N:16]1[CH2:17][C:18](=[O:19])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([C:3](=[N:2][OH:1])[CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=2)[C:14]1=[O:15])[CH:24]=[CH:25][CH3:26]0.01 mol of this urea is dissolved in 150 mL of CH3OH. the pH is adjusted to approximately 10.0 using 25% NaOCH3 solution in CH3OH. The solution is heated to reflux for 2.5 hours, after which time the solvent is removed in vacuo. The residue is washed with cold water and dried in vacuo to yield crude 1-(2-butenyl)-3-[4-(1-hydroxyiminobutyl)phenyl]hydantoin. The hydantoin ispurified by recrystallization from CH3OH: H2O.
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