Hydrochloric Acid → HCID 22996244, compound

HRID 1167297Notes

Reaction equation

HRID 1167297 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:12][CH2:13][CH2:14][CH3:15])[CH:5]=1.[CH2:16]([OH:18])[CH3:17]>>[ClH:1].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8](=[NH:9])[O:18][CH2:16][CH3:17])=[C:6]([O:12][CH2:13][CH2:14][CH3:15])[CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 22996227HCID 22996227, compound

Product 1

HCID 22996244HCID 22996244, compound

Procedure

Hydrogen chloride gas was passed through a solution of 4-methoxy-2-propoxy-benzonitrile (280 mg, 1.464 mmol) in anhydrous ethanol (20 mL) at 0° C. After 1 h, hydrogen chloride gas was stopped and the reaction vessel was sealed with a stopper. After stirring at room temperature for 2 d, the reaction vessel was cooled to 0° C. and the stopper was removed. The solvent was evaporated in vacuo and the residue was triturated in diethyl ether to afford crude ethyl 4-methoxy-2-propoxy-benzimidate hydrochloride. It was dissolved in ethanol (10 mL), and meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (412 mg, 1.464 mmol) and triethylamine (308 μL, 2.194 mmol) were added. The reaction mixture was heated at reflux for 4 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 (2×20 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% ethyl acetate in hexanes to afford 4,5-bis-(4-chloro-phenyl)-2-(4-methoxy-2-propoxy-phenyl)-4,5-dihydro-1H-imidazole (303 mg, 46%). HR-MS (ES, m/z) calculated for C25H25N2O2Cl2 [(M+H)+] 455.1288, observed 455.1293.

Workup

  1. customthe reaction vessel was sealed with a stopper
  2. temperaturethe reaction vessel was cooled to 0° C.
  3. customthe stopper was removed
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-67c916c8ce214bef80d604cd3de82891
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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