Urea, 1-(2-chloroethyl)-3-(1,2,3,4-tetrahydro-1-naphthyl)- → 1-(1,2,3,4-Tetrahydronaphthalen-1-yl)imidazolidin-2-one
Reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:6].CC(C)([O-])C.[K+]>O1CCCC1>[CH:8]1([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1Participants
4
Procedure
To a stirred solution of 3.8 grams (0.015 mole) of 1-(2-chloroethyl)-3-(1,2,3,4-tetrahydro-1-naphthyl)urea in 75 ml. dry tetrahydrofuran is added dropwise a solution of 2.25 grams (0.02 mole) of potassium tert-butoxide in 50 ml. of dry tetrahydrofuran under a nitrogen atmosphere. The reaction is then allowed to proceed at ambient temperature overnight. The mixture is then evaporated at reduced pressure. The residue is partitioned between water and ether. The ether layer is washed with water, dried, sodium sulfate, and evaporated at reduced pressure. Crystallization of the residue from acetone-ether-hexane gives 0.70 grams of product, melting point 134° to 139.5° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 138° to 141.5° C. Analysis calculated for C13H16N2O: C, 72.19; H, 7.46; N, 12.95. Found: C, 72.04; H, 7.43; N, 12.89.