Reaction equation
[CH2:1]([C:3]1([CH2:12][CH3:13])[C:8](=[O:9])[NH:7][C:6](=[O:10])[NH:5][C:4]1=[O:11])[CH3:2].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1.[C:26](=[O:29])([O-])[O-].[K+].[K+].CN(C)[CH:34]=[O:35]>>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:7]2[C:8](=[O:9])[C:3]([CH2:1][CH3:2])([CH2:12][CH3:13])[C:4](=[O:11])[N:5]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:26]([O:35][CH3:34])=[O:29])=[CH:19][CH:18]=3)[C:6]2=[O:10])=[CH:19][CH:18]=1)=[O:25]Participants
Procedure
A mixture of 46.05 g (0.25 mol) of diethylbarbituric acid, 96.9 g (0.525 mol) of 4-chloromethylbenzoic acid methyl ester and 38 g (0.275 mol) of finely ground, anhydrous potassium carbonate in 450 ml of dimethylformamide is stirred at room temperature and is heated to 100° C over the course of 2 hours. The reaction solution is kept at 100° C for one hour and the temperature is then raised to 135° C, whilst stirring. Stirring is continued for a further 4 hours at 135° C and the reaction mixture is then filtered, while still hot. 77.8 g of colourless crystals can be isolated from the cooled filtrate and concentrating the mother liquor gives a further 42 g of a syrup which crystallises (total yield of crude material: 119.8 g; theory: 120.1 g).
Workup
- temperatureis heated to 100° C over the course of 2 hours
- temperaturethe temperature is then raised to 135° C
- stirringwhilst stirring
- stirringStirring
- waitis continued for a further 4 hours at 135° C
- filtrationthe reaction mixture is then filtered
Sources & evidence
- ORD record
- ord-db56db7247c5409196530280c37a6b7f
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04130560
Linked notes
Loading…