Hydrochloric Acid → Ethyl 2,4-dimethoxy-benzimidate hydrochloride

HRID 1582461Notes

Reaction equation

HRID 1582461 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[CH2:14]([OH:16])[CH3:15]>>[ClH:1].[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[C:6](=[NH:7])[O:16][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 777502,4-Dimethoxybenzonitrile

Product 1

HCID 22721088Ethyl 2,4-dimethoxy-benzimidate hydrochlorideYield 57%

Procedure

Hydrogen chloride gas was passed through a solution of 2,4-dimethoxy-benzonitrile (5.20 g, 32 mmol) in anhydrous ethanol (200 mL) at 0° C. After 7 h, hydrogen chloride gas was stopped and the reaction mixture was stirred at room temperature overnight. The solvent was removed and the residue was triturated in diethyl ether to afford ethyl 2,4-dimethoxy-benzimidate hydrochloride (4.5 g, 57%). It was used without further purification.

Workup

  1. customThe solvent was removed
  2. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-8df2d3d2fdad44ba9f89268a3002e98f
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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