Phosphorus oxychloride → 4-(4-Chloro-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate
Reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=O)[NH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:24][C:25](=[O:27])[CH3:26])(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:30])=O>>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([Cl:30])=[N:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[CH:7][C:6]=1[O:24][C:25](=[O:27])[CH3:26])(=[O:3])[CH3:2]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
4-(3,4-Dihydro-4-oxo-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate (6.8 g) (18.7 mmol) are dissolved in 150 ml of phosphorus oxychloride. After stirring at 100° C. for 6 hours the mixture is concentrated in a vacuum at 50° C. and the residue is dried in a vacuum. Now, dichloromethane and ice/water are added thereto and, after good intermixing, the dichloromethane phase is separated. After drying over sodium sulphate and distilling off the solvent the product is crystallized from ethanol. The product is filtered off and washed with ethanol/diethyl ether. There are obtained 6 g of 4-(4-chloro-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate as white crystals of m.p. 152°-153° C.
Workup
- concentrationis concentrated in a vacuum at 50° C.
- customthe residue is dried in a vacuum
- additionNow, dichloromethane and ice/water are added
- customafter good intermixing, the dichloromethane phase is separated
- dry with materialAfter drying over sodium sulphate
- distillationdistilling off the solvent the product
- customis crystallized from ethanol
- filtrationThe product is filtered off
- washwashed with ethanol/diethyl ether
Sources & evidence
- ORD record
- ord-2e5fd8bb9688462ca324f44ae0bd976a
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05438052
Reaction notes
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