Sodium Bicarbonate → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(3-quinolinylmethyl)-
Reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[OH:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1Participants
3
Procedure
In 10 ml of c-HCl was dissolved 730 mg (1.36 mmol)of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (100b); the mixture was refluxed with heating for 1 hour, and worked up. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added, extracted with methylene chloride, the extract was washed with water and dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate)to give 500 mg of 2-hydroxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (109)(yield 83%). mp 174-175° C.
Workup
- temperaturethe mixture was refluxed
- temperaturewith heating for 1 hour
- extractionextracted with methylene chloride
- washthe extract was washed with water
- customdried
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate)to
Sources & evidence
- ORD record
- ord-3f8cf6e6dbe84cbaa1236fb713babc28
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05910506
Reaction notes
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