Hydrochloric Acid → HCID 21896882, compound

HRID 719122Notes

Reaction equation

HRID 719122 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].[CH2:15]([OH:17])[CH3:16]>>[ClH:1].[CH2:2]([O:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:6]=1[C:7](=[NH:8])[O:17][CH2:15][CH3:16])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 21896905224789-17-7

Product 1

HCID 21896882HCID 21896882, compoundYield 79%

Conditions

Temperature
-10 °C

Procedure

Hydrogen chloride gas was passed through a solution of 2-ethoxy-4-methoxy-benzonitrile (6.3 g, 35.55 mmol) in anhydrous ethanol (70 mL) cooled to −10° C. After 30 min, hydrogen chloride gas was stopped and the reaction mixture was stirred at room temperature in a closed reaction vessel for 4 d. 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-ethoxy-4-methoxy-benzimidate hydrochloride (7.3 g, 79%). 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-1cbf5cb58a3f420389ba7b092e4888e9
Source dataset
uspto-grants-2006_11
Patent number
US07132421B2

Reaction notes

Loading…