Thionyl Chloride → 4-(Chloromethyl)-2-[2-(2-chlorophenyl)ethenyl]-5-methyl-1,3-oxazole
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]=[CH:5][C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11]O)[N:10]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH2:11][C:9]1[N:10]=[C:6]([CH:5]=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[Cl:1])[O:7][C:8]=1[CH3:13]Participants
3
Procedure
2-(2-Chlorostyryl)-4-hydroxymethyl-5-methyloxazole (3.6 g) was added portionwise to thionyl chloride (18 ml) with ice-cooling and stirring. The mixture was stirred at room temperature for 20 minutes and the thionyl chloride was distilled off. To the residue was added aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off to give 4-chloromethyl-2-(2-chlorostyryl)-5-methyloxazole as crystals; yield 3.65 g (99.5%). Recrystallization from ethyl ether gave colorless needles melting at 109°-110° C.
Workup
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 20 minutes
- distillationthe thionyl chloride was distilled off
- additionTo the residue was added aqueous sodium hydrogen carbonate
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was then distilled off
Sources & evidence
- ORD record
- ord-ee62ee8204ed4884b77c4ee025a7c2d4
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04602027
Reaction notes
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