Hydrochloric Acid → 2-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid

HRID 1750209Notes

Reaction equation

HRID 1750209 reaction equation
C[O:2][C:3]([C:5]1[CH:25]=[CH:24][C:8]2[N:9]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:10]([CH2:12][C:13]3[S:14][C:15]([Cl:18])=[CH:16][CH:17]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Li+].O.Cl>CO>[Cl:18][C:15]1[S:14][C:13]([CH2:12][C:10]2[N:9]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:8]3[CH:24]=[CH:25][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 867144192-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 867144202-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acidYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.57 g of 2-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl ester in 3 ml of methanol were added 0.08 g of lithium hydroxide and 1 ml of water. The reaction was heated to reflux for 1 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 product precipitated after treatment with diethylether and 0.30 g (55%) of 2-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid were obtained.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 h
  3. extractionwas extracted with ethyl acetate three times
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe product precipitated after treatment with diethylether

Sources & evidence

ORD record
ord-523f5c81a29443cfb8923d5b809ebb50
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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