Hydrochloric Acid → HCID 178487468, compound

HRID 1368526Notes

Reaction equation

[CH3:1][O:2][C:3]([C:17]1[N:18]=[CH:19][N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=1)([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[CH3:4].Cl.N1C=CC=CC=1.Cl>CO>[CH3:1][O:2][C:3]([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

4-[1-Methoxy-1-(6-methoxynaphthalen-2-yl)ethyl]-1-trityl-1H-imidazole (1.5 g) and pyridine hydrochloride (500 mg) were dissolved in methanol (8 ml). The solution was stirred at 60° C. for 2 h. After cooling, 1 N-hydrochloric acid was added to the solution, and precipitate was filtered off. The filtrate was washed with ether and neutralized with potassium carbonate. The filtrate was extracted with ethyl acetate, washed with saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=30:1) to give the titled compound (0.33 g) as a colorless powder.

Workup

temperatureAfter cooling
filtrationwas filtered off
washThe filtrate was washed with ether and neutralized with potassium carbonate
extractionThe filtrate was extracted with ethyl acetate
washwashed with saturated aqueous solution of sodium chloride
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=30:1)

Sources & evidence

ORD record: ord-5de2ff09055a4806a295290b8ab9380f
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Reaction notes

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