Hydrochloric Acid → HCID 22996246, compound
Reaction equation
[ClH:1].[CH2:2]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH3:15])=[C:10]([CH:13]=1)[C:11]#[N:12])[CH3:3].[CH2:16]([OH:18])[CH3:17]>>[ClH:1].[CH2:2]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH3:15])=[C:10]([CH:13]=1)[C:11](=[NH:12])[O:18][CH2:16][CH3:17])[CH3:3]Participants
Procedure
Hydrogen chloride gas was passed through a solution of 5-ethoxymethyl-2-methoxy-benzonitrile (181 mg, 0.947 mmol) in anhydrous ethanol (30 mL) at room temperature. After 2 h, hydrogen chloride gas was stopped and the reaction vessel was sealed. After stirring at room temperature for 12 h, the reaction vessel was cooled to 0° C. and opened. The solvent was evaporated in vacuo to dryness to afford crude ethyl 5-ethoxymethyl-2-methoxy-benzimidate hydrochloride. meso-1,2-Bis-(4-chloro-phenyl)-ethane-1,2-diamine (253 mg, 0.9 mmol), triethylamine (186 μL, 1.5 mmol) and ethanol (10 mL) were added and the resulting mixture was heated at reflux for 12 h. The solvent was removed and the residue was taken up in methylene chloride (2 mL) and sodium bicarbonate solution (2 mL). The product was extracted with methylene chloride (2×30 mL). The organic layers were washed with brine (1×5 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 70-100% ethyl acetate in hexanes to afford 4,5-bis-(4-chloro-phenyl)-2-(5-ethoxymethyl-2-methoxy-phenyl)-4,5-dihydro-1H-imidazole (136 mg, 33%). LR-MS (APCI): 455 [(M+H)+].
Workup
- customthe reaction vessel was sealed
- temperaturethe reaction vessel was cooled to 0° C.
- customThe solvent was evaporated in vacuo to dryness
Sources & evidence
- ORD record
- ord-92c5aa2c6221435aa67af8d5cccca6c6
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06617346B1
Reaction notes
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