Hydrochloric Acid → 2-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1750238Notes

Reaction equation

HRID 1750238 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH3:17])=[C:6]([NH:18][C:19](=O)[CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=1.Cl.O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]3[CH3:17])[C:19]([CH2:20][C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[N:18][C:6]=2[CH:5]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 867144453-(2-Furan-2-yl-acetylamino)-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester

Product 1

HCID 867144462-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.48 g 3-(2-Furan-2-yl-acetylamino)-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester with 15 ml of 4M hydrochloric acid in dioxane were heated in a microwave reactor to 130° C. for 15 min. Water was added to the reaction mixture and the pH was adjusted to 7 by the addition of saturated sodium bicarbonate solution. The phases were separated, and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate, concentrated and 1.31 g (93%) of 2-Furan-2-ylmethyl-1-(2-methyl-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid methyl ester were obtained.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05cb8cc9a9944122b1fbc6f10eaf3d7b
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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