Hydrochloric Acid → 1-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750205Notes

Reaction equation

HRID 1750205 reaction equation
C[O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]2[N:9]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[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].CO.[OH-].[Na+].Cl>C1COCC1>[CH2:19]([CH:18]([N:9]1[C:8]2[CH:23]=[CH:24][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[C:10]1[CH2:12][C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:21][CH3:22])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 867144161-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 867144171-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.30 g of 1-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester 12 ml of methanol and 22 ml THF 22 ml of 1 M aqueous sodium hydroxide solution were added and the reaction was stirred 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. 4.83 g (85%) of 1-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid were obtained.

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

Sources & evidence

ORD record
ord-866b13c9fb3b4db0a501e5b778dbc8ff
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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