Chloroform → HCID 22616979, compound

HRID 843240Notes

Reaction equation

HRID 843240 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[N:4]=[C:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].[C:21]([O-:24])(O)=O.[Na+].C(Cl)(Cl)Cl>C(O)(=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[C:9]([CH:21]=[O:24])=[CH:10][CH:5]=[CH:6][CH:7]=3)[C:5]=2[N:4]=[C:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 11173178HCID 11173178, compound

Product 1

HCID 22616979HCID 22616979, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ceric ammonium nitrate (2.19 g, 4.0 mmol) in acetic acid (10 mL, 50%) was added to a stirred solution of N-methyl-4-methyl-2-(2-nitrophenyl)-benzimidazole (0.27 g, 1.0 mmol) in same acid (5.0 mL, 50%) dropwise at 90° C. and the mixture was stirred for 6 hours. The mixture was then cooled to room temperature, neutralized with saturated NaHCO3 to PH=7-8,extracted with CHCl3 and the extract 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 (115 mg, 42%) as a light-yellow solid. Rf=0.28 (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 C15H11N3O3 281.0800, found 281.0814.

Workup

  1. dry with materialthe extract dried over Na2SO4
  2. concentrationConcentration
  3. customa rotary evaporator and subsequent column chromatography on silica gel

Sources & evidence

ORD record
ord-30e4fe4566744c65bef75e884784c2f1
Source dataset
uspto-grants-2002_04
Patent number
US06376664B1

Reaction notes

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