[Cl-].[Li+].[CH2:3]([CH:5]1[O:7][CH2:6]1)[Cl:4].[CH3:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=O)=[CH:13][CH:12]=1)[CH3:10].[OH2:20]>CN(C)C=O>[Cl:4][CH2:3][CH:5]1[O:7][C:6](=[O:20])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:9]([CH3:10])[CH3:8])=[CH:12][CH:13]=2)[CH2:18]10.2-0.3 grams of lithium chloride was added to a solution of 7 grams (0.076 mole) epichlorohydrin in 30 ml dimethylformamide at 90° C. Heating was discontinued, and a solution of 12.25 grams (0.076 mole) 4(1-methylethyl)phenylisocyanate in 10 ml dimethylformamide was added dropwise at such a rate that the reaction temperature did not exceed 110° C. When the addition was complete heat was reapplied and the reaction solution was stirred at 90° C. for 3 hours. The solution was then added in a slow stream to a vigorously stirred mixture of ice and water, about 200 ml total volume. The reaction product solidified and was recovered by filtration. Recrystallization from methanol afforded an 85% yield of white crystalline material (mp 77°-79° C.).
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