Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:32]([N:35]=[C:36]=[O:37])[CH2:33][CH3:34]>CCCCCC>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:36]([NH:35][CH2:32][CH2:33][CH3:34])=[O:37])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.36 g, 0.0008 mol) in hexane (15 mL) was added propylisocyanate (0.094 mL, 0.085 g, 0.001 mol), and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was then treated with additional propylisocyanate (0.094 mL, 0.085 g, 0.001 mol) and stirred at ambient temperature overnight and then at reflux for 72 hours. The reaction mixture was concentrated under vacuum and the residue was chromatographed using 2:8 hexane-ethyl acetate. The resulting oil was triturated with hexane to give the title compound (0.8 g, 0.00015 mol) as a white solid, mp 78°-80°. 1H NMR (CDCl3) 7.6-7.2(m,10H), 4.4(t,1H,J=7Hz), 3.4-2.9(m,8H), 1.9-1.1(m,19H), 1.0-0.75(m,6H).
Workup
- stirringstirred at ambient temperature overnight
- temperatureat reflux for 72 hours
- concentrationThe reaction mixture was concentrated under vacuum
- customthe residue was chromatographed
- customThe resulting oil was triturated with hexane
Sources & evidence
- ORD record
- ord-b382e4e2bea345c5902d34a8101ba62d
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166214
Linked notes
Loading…