Hydrochloric Acid → 4-Methyl-2-propyl-1H-benzimidazole-6-carboxylic acid methyl ester

HRID 476293Notes

Reaction equation

HRID 476293 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:6]=2[CH:5]=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=1.Cl.[CH3:18]O>>[CH3:18][O:15][C:14]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:6]=2[CH:5]=1)=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 102628317-Methyl-2-propyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 101308354-Methyl-2-propyl-1H-benzimidazole-6-carboxylic acid methyl ester

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.

Workup

  1. additionadded to a round bottom flask
  2. temperatureThe mixture was refluxed for 12 hours
  3. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-31eab2e96aa44fc8913e5e247f48aefa
Source dataset
uspto-grants-2014_01
Patent number
US08637676B2

Reaction notes

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