1,1'-Carbonyldiimidazole → HCID 67916704, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:25][N:26]([CH2:28][C@H:29]1[C@H:34]([OH:35])[CH2:33][CH2:32][CH2:31][NH:30]1)[CH3:27]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:30]2[CH2:31][CH2:32][CH2:33][C@@H:34]([OH:35])[C@@H:29]2[CH2:28][N:26]([CH3:27])[CH3:25])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3,4-dichlorophenylacetic acid (2.59 g) and 1,1'-carbonyldiimidazole (2.42 g) in dry tetrahydrofuran (30 ml) was stirred at room temperature under nitrogen for 20 min. A solution of the product of stage (i) (2.0 g) in dry tetrahydrofuran (10 ml) was added and stirring was continued for 16 h before concentrating the reaction mixture in vacuo. The residue was purified by column chromatography on UGI alumina (2.5" diameter×8") with graded elution from dichloromethane/methanol (98:2) to dichloromethane/methanol (9:1) to give the free base of the title compound as an oil (2.7 g). This oil was dissolved in dry diethyl ether (200 ml) and treated with ethereal hydrogen chloride to precipitate the hydrochloride salt which was crystallised from ethyl acetate/methanol to give the title compound as a crystalline solid (0.42 g), m.p. 185°-186°.
Workup
- concentrationbefore concentrating the reaction mixture in vacuo
- customThe residue was purified by column chromatography on UGI alumina (2.5" diameter×8") with graded elution from dichloromethane/methanol (98:2) to dichloromethane/methanol (9:1)
Sources & evidence
- ORD record
- ord-fa7adce069464a4396d6136809c9d9e7
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05114945
Reaction notes
Loading…