Hydrochloric Acid → HCID 86714429, compound

HRID 1750220Notes

Reaction equation

HRID 1750220 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:10]([CH2:12][C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO.C1COCC1>[CH:19]1([CH2:18][N:9]2[C:8]3[CH:25]=[CH:26][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=[C:10]2[CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86714428HCID 86714428, compound

Product 1

HCID 86714429HCID 86714429, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 13.60 g of 1-Cyclohexylmethyl-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 25 ml of methanol and 100 ml of THF were added 37 ml of 2 M aqueous sodium hydroxide solution. The reaction stirred at rt for 6 h. The reaction mixture was adjusted to pH 4 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 purified by chromatography (silica, heptane/ethyl acetate) to yield 11.1 g (85%) of 1-Cyclohexylmethyl-2-thiophen-2-ylmethyl-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 purified by chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-d4f2ccd8f28f4c69b9a031d93ee72a09
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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