Thionyl Chloride → HCID 22412159, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([CH3:16])=[C:12]([CH2:14]O)[N:13]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[ClH:2].[Cl:19][CH2:14][C:12]1[N:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[NH:10][C:11]=1[CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred slurry of 10.4 g (0.04 mole) of 2-p-chlorophenyl-4-hydroxymethyl-5-methyl-imidazole hydrochloride in 250 ml of chloroform is added 10 g (0.08 mole) of thionyl chloride in CHCl3. The reaction mixture is warmed to reflux for 6 hours with stirring and then cooled to room temperature. White crystals of 4-chloromethyl-2-p-chlorophenyl-5-methylimidazole hydrochloride in 98% yield, m.p., 224°-226° C (dec.) are obtained. This material is collected and dissolved in 50 ml of warm DMSO and added to a solution of 10 g (0.2 mole) of sodium cyanide in 150 ml of hot DMSO. The mixture is warmed to 60° C for 16 hours and then stirred at room temperature for 16 hours. The reaction mixture is poured over 1 liter of ice and stirred. The tan solid that forms is filtered, collected and air-dried. The crude solid is taken up in 2 liters of ether, charcoaled and filtered. Concentration on a steam bath with hexane addition yields pale green crystals of product. Additional recrystallizations from ether-hexane and methylene chloridehexane gives about 4.5 g (49%) of pale yellow crystals of 2-(p-chlorophenyl)-4-cyanomethyl-5-methyl-imidazole, m.p., 163° - 165° C. Treatment with a mineral acid, e.g., hydrochloric, nitric, sulfuric and the like, affords the corresponding acid addition salts.
Workup
- temperatureThe reaction mixture is warmed
- temperatureto reflux for 6 hours
Sources & evidence
- ORD record
- ord-bdb1d62f4f834ec6b0b04932012e75f7
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04093811
Reaction notes
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