Dimethyl Sulfoxide → HCID 19908894, compound
Reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[OH:29].[OH-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:29]Participants
Conditions
- Temperature
- -76 °C
Procedure
Dimethylsulfoxide (8.46 g) was mixed with methylene chloride (35 ml) and cooled to -76° C. with stirring and after dropwise addition of a diluted solution of trifluoroacetic anhydride (19.71 g) in methylene chloride (10 ml), stirred for 1 hour. A solution of of 2-imidazolylcyclohexanol (IVa) (12.0 g) in methylene chloride (100 ml) was added dropwise thereto for 10 minutes. The mixture was made to react at -76°--20° C. for 1.5 hours, cooled to -55° C. and after dropwise addition of triethylamine (30 ml) at -55° C., stirred for 1 hour at -55° C. After addition of a 5% sodium hydroxide solution, the mixture was extracted with methylene chloride. The extract was washed with water, dried and evaporated. The residue was applied to column chromatography on slica gel (100 g). From Chloroform-methanol (100:1) fraction, 2-imidazolyl cyclohexanone (IIa) (2.3 g) was obtained. Mp. 104°-105° C.
Workup
- stirringstirred for 1 hour
- customto react at -76°--20° C. for 1.5 hours
- temperaturecooled to -55° C.
- stirringstirred for 1 hour at -55° C
- extractionthe mixture was extracted with methylene chloride
- washThe extract was washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-2d84b01690794dd19f0f1773dcc7b53e
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091539
Reaction notes
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