Acetic Acid → HCID 69134259, compound

HRID 969538Notes

Reaction equation

HRID 969538 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[CH:16]=[C:15]([O:17]CC2C=CC=CC=2)[C:8]2[N:9]=[C:10]([CH2:13][CH3:14])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].C(O)(=O)C>C(O)C.[Pd]>[CH3:25][N:2]([CH3:1])[C:3]([C:5]1[CH:16]=[C:15]([OH:17])[C:8]2[N:9]=[C:10]([CH2:13][CH3:14])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69134282HCID 69134282, compound

Product 1

HCID 69134259HCID 69134259, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.9 g (26.6 mmol) 7-benzyloxy-2-ethyl-3-methyl-3H-benzimidazole-5-carboxylic acid dimethylamide and 1.8 ml acetic acid in 160 ml ethanol was hydrogenated over 1.7 g 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. The residue was crystallized from acetone to afford 7 g (91%) of the title compound as a white solid. m.p. 193°-199° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was crystallized from acetone

Sources & evidence

ORD record
ord-97ae15a3e2eb44d4b8536a24923f9446
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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