HCID 68936251, compound → HCID 68939750, compound

HRID 2377145Notes

Reaction equation

HRID 2377145 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:13]2[CH:23]=[CH:22][C:16]3[N:17]([CH3:21])[C:18]([CH3:20])=[N:19][C:15]=3[CH:14]=2)[OH:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]([C:13]2[CH:23]=[CH:22][C:16]3[N:17]([CH3:21])[C:18]([CH3:20])=[N:19][C:15]=3[CH:14]=2)=[O:12])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 68936251HCID 68936251, compound

Product 1

HCID 68939750HCID 68939750, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazol-5-yl)-methanol (2.1 g, 6.7 mmol) and MnO2 (2.9 g, 33.6 mmol) in CH2Cl2 (300 mL) was stirred at room temperature for 17 h. The mixture was filtered through celite and solvent was removed. The crude product was slurried with ether to afford (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazol-5-yl)-methanone (2.0 g, 99%) as an off white solid: 1H NMR (DMSO-d6) δ 7.90 (s, 1H), 7.71-7.62 (m, 2H), 6.80 (s, 3H), 3.80 (s, 3H), 3.35 (s, 3H), 2.58 (s, 3H); 13C NMR (DMSO-d6) δ 195.28, 160.17, 154.83, 141.54, 140.27, 139.15, 130.15, 123.50, 120.73, 109.70, 107.19, 103.62, 55.47, 29.96, 13.52.

Workup

  1. filtrationThe mixture was filtered through celite and solvent
  2. customwas removed

Sources & evidence

ORD record
ord-3dac726da66e4395bf7ab8fbeebf3f82
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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