Sodium Bicarbonate → (1-(2-Hydroxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)methanol

HRID 1857784Notes

Reaction equation

C([O:8][CH2:9][C:10]1[N:11]([CH2:27][CH:28]([OH:30])[CH3:29])[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+]>Cl>[Cl:26][C:21]1[CH:20]=[C:19]([S:18][C:12]2[N:11]([CH2:27][CH:28]([OH:30])[CH3:29])[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:17])[CH3:16])[CH:24]=[C:23]([Cl:25])[CH:22]=1

Participants

Conditions

Temperature: 110 °C

Procedure

In 55 ml of concentrated hydrochloric acid was dissolved 13.4 g (28.7 mmol) of the alcohol (140a), and after the mixture was stirred with heating at 110° C. for 2 hours, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture. The mixture was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (methylene chloride-ethyl acetate=9:1), the oil was treated with ether and crystallized to provide 9.1 g (yield 84%) of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole (141a). mp 159-161° C.

Workup

distillationThe mixture was distilled off under reduced pressure
extractionthe residue was extracted with ethyl acetate
washThe extract was washed with water
customdried
distillationthe solvent was distilled off
customThe residue was purified by silica gel column chromatography (methylene chloride-ethyl acetate=9:1)
additionthe oil was treated with ether
customcrystallized

Sources & evidence

ORD record: ord-0199b75303d940a79668a41f5ec8f049
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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