Hydrochloric Acid → Ethyl 2-isopropoxy-4-methoxybenzimidate hydrochloride

HRID 1167304Notes

Reaction equation

HRID 1167304 reaction equation
[ClH:1].[CH:2]([O:5][C:6]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9])([CH3:4])[CH3:3].[CH2:16]([OH:18])[CH3:17]>>[ClH:1].[CH:2]([O:5][C:6]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:7]=1[C:8](=[NH:9])[O:18][CH2:16][CH3:17])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 227210812-Isopropoxy-4-methoxybenzonitrile

Product 1

HCID 21896893Ethyl 2-isopropoxy-4-methoxybenzimidate hydrochlorideYield 99%

Conditions

Temperature
-10 °C

Procedure

Hydrogen chloride gas was passed through a solution of 2-isopropoxy-4-methoxy-benzonitrile (11.5 g, 60.14 mmol) in anhydrous ethanol (250 mL) cooled to −10° C. After 45 min, hydrogen chloride gas was stopped and the reaction mixture was stirred at room temperature in a closed reaction vessel for 2 weeks. The reaction vessel was cooled to 0° C. before the stopper was removed. Argon gas was passed through the solution to remove excess hydrogen chloride gas. The solvent was evaporated and the residue was triturated in diethyl ether (100 mL) to afford ethyl 2-isopropoxy-4-methoxy-benzimidate hydrochloride (16.3 g, 99%). It was used without further purification.

Workup

  1. temperatureThe reaction vessel was cooled to 0° C. before the stopper
  2. customwas removed
  3. customto remove excess hydrogen chloride gas
  4. customThe solvent was evaporated
  5. customthe residue was triturated in diethyl ether (100 mL)

Sources & evidence

ORD record
ord-569752e827a34fd0a523bb50db91fa0e
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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