1,1'-Carbonyldiimidazole → HCID 10199947, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[O:5][C:6]1[C:7]([CH2:18][CH3:19])=[N:8][N:9]([CH2:13][C:14]([NH:16][NH2:17])=[O:15])[C:10]=1[CH2:11][CH3:12].[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[O:5][C:6]1[C:7]([CH2:18][CH3:19])=[N:8][N:9]([CH2:13][C:14]2[O:15][C:24](=[O:25])[NH:17][N:16]=2)[C:10]=1[CH2:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of the hydrazide (275 mg, 0.77 mmol) of Example 11 and 1,1′-carbonyl diimidazole 187 mg, 1.16 mmol) in dioxane (50 ml) was heated under reflux for 18 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (50 ml) and washed with water (25 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (112 mg) as a white solid m.p. 138-142° C.