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

HRID 1750208Notes

Reaction equation

HRID 1750208 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:6]([NH:16][C:17](=O)[CH2:18][C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH:5]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:17]([CH2:18][C:19]3[S:20][C:21]([Cl:24])=[CH:22][CH:23]=3)=[N:16][C:6]=2[CH:5]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867144183-[2-(5-Chloro-thiophen-2-yl)-acetylamino]-4-(1-ethyl-propylamino)-benzoic acid methyl ester

Product 1

HCID 867144192-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 77.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.99 g 3-[2-(5-Chloro-thiophen-2-yl)-acetylamino]-4-(1-ethyl-propylamino)-benzoic acid methyl ester were reacted with 10 ml of 4M hydrochloric acid in dioxane in a microwave reactor at 130° C. for 15 min. The reaction was concentrated. The residue was dissolved in ethyl actate, washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulphate and concentrated to yield 0.73 g (77%) of 2-(5-Chloro-thiophen-2-ylmethyl)-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl ester.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was dissolved in ethyl actate
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e0ff9c917b145a294249ccd15ee25bb
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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