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

HRID 1750204Notes

Reaction equation

HRID 1750204 reaction equation
[CH3:1][O:2][C:3](=[O:25])[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[O:20][CH:21]=[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[O:20][CH:21]=[CH:22][CH:23]=3)=[N:16][C:6]=2[CH:5]=1)=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867144154-(1-Ethyl-propylamino)-3-(2-furan-2-yl-acetylamino)-benzoic acid methyl ester

Product 1

HCID 867144161-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl esterYield 105.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.70 g of 4-(1-Ethyl-propylamino)-3-(2-furan-2-yl-acetylamino)-benzoic acid methyl ester were dissolved in 25 ml of dry dioxane and 50 ml of 4M hydrochloric acid in dioxane were added. The reaction was heated to reflux for 10 h and concentrated to yield 4.70 g (100%) of 1-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid methyl ester which was used in the next step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 10 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eb137e6675c64616a5add12648a7c622
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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