Hydrochloric Acid → 5-Chloro-2-methoxy-benzimidic acid ethyl ester

HRID 28550Notes

Reaction equation

HRID 28550 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:8](=[NH:9])[C:7]1[CH:10]=[C:3]([Cl:2])[CH:4]=[CH:5][C:6]=1[O:11][CH3:12])[CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 28009795-Chloro-2-methoxybenzonitrile

Product 1

HCID 668514685-Chloro-2-methoxy-benzimidic acid ethyl esterYield 56%

Procedure

Hydrogen chloride gas (˜200 mmol) was passed into a solution of 5-chloro-2-methoxy-benzonitrile(1.68 g, 10.0 mmol) in ethanol (50 ml). After stirring for 48 hours, the mixture was concentrated under reduced pressure. The residue was treated with ethyl acetate (25 ml) and stirred for 1 hour. Filtration provided 5-chloro-2-methoxy-benzimidic acid ethyl ester (1.20 g, 56% yield) as a white powder.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was treated with ethyl acetate (25 ml)
  3. stirringstirred for 1 hour
  4. filtrationFiltration

Sources & evidence

ORD record
ord-87f145894fa347679a1ceb40b0057847
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

Loading…