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

HRID 1582472Notes

Reaction equation

HRID 1582472 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 702Ethanol2×HCID 227210812-Isopropoxy-4-methoxybenzonitrile

Product 1

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

Procedure

Hydrogen chloride gas was passed through a solution of 2-isopropoxy-4-methoxybenzonitrile (13.2 g, 69 mmol) in absolute ethanol (200 mL) in a pressure tube for 1 h at −10° C. The tube was sealed and stirred at room temperature for 7 d. The tube was cooled to −10° C. and more ethanol (100 mL) was added. Hydrogen chloride gas was passed through it for additional 30 min at −10° C. The tube was resealed and stirred at room temperature for 7 d. Evaporation of the solvents and trituration of the residue in diethyl ether gave ethyl 2-isopropoxy-4-methoxy-benzimidate hydrochloride as a white solid (17.5 g, 99%). It was used without further purification.

Workup

  1. customThe tube was sealed
  2. temperatureThe tube was cooled to −10° C.
  3. stirringstirred at room temperature for 7 d
  4. customEvaporation of the solvents and trituration of the residue in diethyl ether

Sources & evidence

ORD record
ord-e8edfd28bcdc4ee9b44224c07b475e0a
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

Loading…