Hydrochloric Acid → HCID 58817962, compound

HRID 1643202Notes

Reaction equation

Cl.[CH2:2]([N:6]1[C:10](CC#N)=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]=[C:7]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][CH2:4][CH3:5].O.[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28]>CO>[CH3:31][O:30][C:27](=[O:29])[CH2:28][C:10]1[N:6]([CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:8][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrogen chloride gas is bubbled into solution of (3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-acetonitrile (187) (640 mg, 2.03 mmol) in methanol (30 mL) at 0° C. for 10 minutes, followed by stirring for 30 minutes. Water (0.0365 ml, 2.03 mmol) is then added and the reaction refluxed at 80° C. for 2 hours. The methanol is then removed in vacuo, the reaction crude is dissolved in ethyl acetate (100 mL), and the organic layer is washed with saturated sodium bicarbonate (1×100 mL), brine (1×100 mL), and dried over magnesium sulfate. The sample is filtered, concentrated and purified by flash chromatography on SiO2 using an eluent of 2:3 ethyl acetate:hexane to afford (3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-acetic acid methyl ester (188) as a colorless oil.

Workup

customThe methanol is then removed in vacuo
customthe reaction crude
washthe organic layer is washed with saturated sodium bicarbonate (1×100 mL), brine (1×100 mL)
dry with materialdried over magnesium sulfate
filtrationThe sample is filtered
concentrationconcentrated
custompurified by flash chromatography on SiO2 using an eluent of 2:3 ethyl acetate

Sources & evidence

ORD record: ord-df59204a627a4a6aba387622404b8f18
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119665B2

Reaction notes

Loading…