Acetic Acid → HCID 69134430, compound

HRID 969530Notes

Reaction equation

HRID 969530 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([C:5]1[CH:17]=[C:16]([O:18]CC2C=CC=CC=2)[C:8]2[N:9]=[C:10]([CH3:15])[N:11]([CH2:12][O:13][CH3:14])[C:7]=2[CH:6]=1)=[O:4].C(O)(=O)C>C(O)C.[Pd]>[CH3:26][N:2]([CH3:1])[C:3]([C:5]1[CH:17]=[C:16]([OH:18])[C:8]2[N:9]=[C:10]([CH3:15])[N:11]([CH2:12][O:13][CH3:14])[C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69136056HCID 69136056, compound

Product 1

HCID 69134430HCID 69134430, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.8 g (5.0 mmol) 7-benzyloxy-3-methoxymethyl-2-methyl-3H-benzimidazole-5-carboxylic acid dimethylamide and 270 μl acetic acid in 150 ml ethanol was hydrogenated over 240 mg 10% Pd/C in autoclave (5 bar H2) at 50° C. for 18 h. The catalyst was filtered off and the filtrate was concentrated in vacuo and crystallized from ethyl acetate-petroleum ether to afford 0.8 g (62%) of the title compound as a white solid. m.p. 173°-183° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customcrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-861f91afce354c1aa278063292d9619a
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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