Methanol → HCID 20068404, compound
Reaction equation
[Na].Cl.[Cl:3][CH2:4][C:5]1[N:9]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH:8]=[N:7][CH:6]=1.[CH3:18][OH:19]>>[ClH:3].[CH3:18][O:19][CH2:4][C:5]1[N:9]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH:8]=[N:7][CH:6]=1Participants
Procedure
To a stirred solution of 1.38 parts of sodium in 40 parts of methanol were added 3.84 parts of 5-(chloromethyl)-1-(1-phenylethyl)-1H-imidazole monohydrochloride. Stirring was continued for one hour at reflux. The reaction mixture was evaporated. Water was added to the residue and the product was extracted with 2,2'-oxybispropane. The extract and dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 4-methyl-2-pentanone. The salt was filtered off and dried, yielding 1.8 parts of 5-(methoxymetyl)-1-(1-phenylethyl)-1H-imidazole monohydrochloride; mp. 166.3° C. (compound 8.37).
Workup
- temperatureat reflux
- customThe reaction mixture was evaporated
- additionWater was added to the residue
- extractionthe product was extracted with 2,2'-oxybispropane
- extractionThe extract
- customdried
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- filtrationThe salt was filtered off
- customdried
Sources & evidence
- ORD record
- ord-ba7faa80f3d6497f9fb5f402ebb1bb0b
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04878940
Reaction notes
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