Hydrochloric Acid → 2-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid

HRID 1750239Notes

Reaction equation

HRID 1750239 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]3[CH3:24])[C:10]([CH2:12][C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][C:10]1[N:9]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[CH3:24])[C:8]2[CH:25]=[CH:26][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867144462-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 867144472-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acidYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.30 g of 2-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid methyl ester in 15 ml of methanol were added 6 ml of 2 M aqueous sodium hydroxide solution. The reaction stirred at it for 16 h. The reaction mixture was adjusted to pH 5 by the addition of 2M aqueous hydrochloric acid and was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was precipitated using heptane to yield 0.68 g (54%) of 2-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid.

Workup

  1. extractionwas extracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was precipitated

Sources & evidence

ORD record
ord-20de9b9b40f24adda60a27ba8cd8540a
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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