Potassium bisulfate → HCID 178424781, compound

HRID 2372434Notes

Reaction equation

Cl.C([N:9]1[C:13]([CH2:14][CH2:15][C:16](O)([CH2:27][CH2:28][C:29]2[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:36])[CH2:17][CH2:18][C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])=[CH:12][N:11]=[CH:10]1)C1C=CC=CC=1.S([O-])(O)(=O)=O.[K+]>C(O)C>[CH3:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=1[CH2:18][CH2:17][CH:16]([CH2:27][CH2:28][C:29]1[C:30]([CH3:36])=[CH:31][CH:32]=[CH:33][C:34]=1[CH3:35])[CH2:15][CH2:14][C:13]1[N:9]=[CH:10][NH:11][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4,0 g of 1-benzyl-5-[5-(2,6-dimethylphenyl)-3-hydroxy-3-(2,6-dimethylphenylethyl)pentyl]-1H-imidazole hydrochloride and 20 g of kalium hydrogen sulfate is combined and the mixture is heated for 6 hours at 150° C. Ethanol (40 ml) is added and the mixture is filtered. 20 ml of conc. hydrochloric acid is added and the mixture is hydrogenated palladium on carbon (10%) as catalyst until the hydrogen consumption ceases. The reaction mixture is filtered, water is added and the mixture is made alkaline with sodium hydroxide. The product is then extracted into toluene, which is washed with water, and evaporated to dryness. The residue which is the product as base, is converted to nitrate with nitric acid in water. M.p. 147°-150° C.

Workup

filtrationthe mixture is filtered
addition20 ml of conc. hydrochloric acid is added
customuntil the hydrogen consumption ceases
filtrationThe reaction mixture is filtered
additionwater is added
extractionThe product is then extracted into toluene, which
washis washed with water
customevaporated to dryness

Sources & evidence

ORD record: ord-54cc81903c23464d91787b5ba33bd67a
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098923

Reaction notes

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