Reaction #1583890

ord-3158337acf8c4c2ba2f34ad7ea8fb3f5

Reaction equation

CCCc1nc2c(C)cc(C(=O)O)cc2[nH]1
7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid
CO
MeOH
Cl
hydrogen chloride
CCCc1nc2c(C)cc(C(=O)OC)cc2[nH]1
title compound
CCCc1nc2c(C)cc(C(=O)OC)cc2[nH]1
7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic Acid Methyl Ester

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONadded to a round bottom flask
  2. 2
    TemperatureThe mixture was refluxed for 12 hours
  3. 3
    Concentrationthen concentrated under reduced pressure

Procedure

7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30.0 g, 137 mmol) was dissolved in MeOH (550 mL) and added to a round bottom flask, followed by the addition of 20 mL of a hydrogen chloride solution (30:70, conc. HCl:water). The mixture was refluxed for 12 hours then concentrated under reduced pressure to afford the title compound as a yellow solid (31.8 g, 137 mmol). MS m/z: [M+H+] calcd for C13H16N2O2, 233.12. found 233.2.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198899B2uspto-grants-2015_12