Benzoyl chloride → [(2-Benzoyloxy-5-chloro-alpha-phenylbenzyliden)amino] malonic acid diethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([N:11]=[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[OH:20])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([N:11]=[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:27])[CH3:10]Participants
Procedure
A solution of 7.8 g. of [(5-chloro-2-hydroxy-α-phenylbenzyliden)amino] malonic acid diethyl ester in 15 ml. of pyridine is treated at 10°-15° C. with 3.5 ml. of benzoyl chloride. The mixture is stirred at room temperature for 1 hour and then poured on to 150 ml. of ice-water. The separated oil product is extracted with ehter and the organic phase washed with water, then with 2-N sodium carbonate solution and finally with water. After drying over sodium sulfate and evaporation of the solvent, the oily residue is triturated with hexane, crystallization setting in. There is obtained [(2-benzoyloxy-5-chloro-α-phenylbenzyliden)amino] malonic acid diethyl ester in the form of colorless crystals, having a melting point of 108°-110° C. Recrystallization from ethanol increases the melting point to 109°-111° C.
Workup
- additionpoured on to 150 ml
- extractionThe separated oil product is extracted with ehter
- washthe organic phase washed with water
- dry with materialAfter drying over sodium sulfate and evaporation of the solvent
- customthe oily residue is triturated with hexane, crystallization setting in
Sources & evidence
- ORD record
- ord-f9e4527bd1d9404eb646edac342f64d6
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04089875
Reaction notes
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