Water → HCID 22616979, compound

HRID 843237Notes

Reaction equation

HRID 843237 reaction equation
Br[CH:2](Br)[C:3]1[C:11]2[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:18]([O-:20])=[O:19])[N:8]([CH3:21])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH2:23]>O1CCOCC1.[Ag]>[CH3:21][N:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]3[C:5]([CH:6]=[O:23])=[CH:4][CH:3]=[CH:11][CH:7]=3)[C:11]=2[N:10]=[C:9]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 962WaterHCID 11258809HCID 11258809, compound

Product 1

HCID 22616979HCID 22616979, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of silver hyperchlorate (57 mg, 0.27 mmol) in water (2 mL) was added to a solution of 4-dibromomethyl-N-methyl-2-(2-nitrophenyl)-benzimidazole (39 mg, 0.9 mmol) in 1,4-dioxane (2 mL). The mixture was refluxed for 5 h to afford a grey suspension. After cooling to room temperature, the precipitate was filtered off through a pad of celite and washed with ethyl acetate. The filtrate was washed with water and brine, dried over Na2SO4. Concentration using a rotary evaporator and subsequent column chromatography on silica gel using hexane/ethyl acetate (1:3) as the eluent to give N-methyl-2-(2-nitrophenyl)-benzimidazole-4-benzaldehyde (24 g, 93%) as a light-yellow solid. Rf=0.23 (hexane/ethyl acetate=1:3); 1H NMR (250 MHz, CDCl3) δ 3.68 (s, 3H), 7.47 (t, J=7.8 Hz, 1H), 7.66-7.74 (m, 2H), 7.77-7.86 (m, 2H). 7.90 (d, J=7.6 Hz, 1H), 8.28 (dd, J,=7.9 Hz, J2 =1.5 Hz, 1H), 10.81 (s, 1H). HRMS: Calcd for C1H11N3O3 281.0800, found 281.0814.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. customto afford a grey suspension
  3. filtrationthe precipitate was filtered off through a pad of celite
  4. washwashed with ethyl acetate
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration
  8. customa rotary evaporator and subsequent column chromatography on silica gel

Sources & evidence

ORD record
ord-a5eccee358e94ec6a3a110e985656677
Source dataset
uspto-grants-2002_04
Patent number
US06376664B1

Reaction notes

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