Water → 1-Methyl-2-(2-nitrophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal

HRID 843233Notes

Reaction equation

HRID 843233 reaction equation
[CH2:1]1[O:23][CH:4]([C:5]2[C:13]3[NH:12][C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-:22])=[O:21])=[N:10][C:9]=3[CH:8]=[CH:7][CH:6]=2)[O:3][CH2:2]1.[H-].[Na+].[CH3:26]I.O>C1COCC1>[CH2:1]1[O:23][CH:4]([C:5]2[C:13]3[N:12]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-:22])=[O:21])[N:10]([CH3:26])[C:9]=3[CH:8]=[CH:7][CH:6]=2)[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526574HCID 178526574, compound

Product 1

HCID 154902661-Methyl-2-(2-nitrophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-nitrophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal 5 (4.53 g, 14.6 mmol) in dry THF (20 mL) was added to a stirring suspension of NaH (0.640 g, 60% dispersion in mineral oil, 16.0 mmol) in dry THF (50 mL) at 0° C. under N2. The mixture was then allowed to warm to room temperature for 1 hour resulting in an orange solution. Methyl iodide (4.58 mL, 72.8 mmol) was syringed into the above mixture at room temperature under N2. This mixture was stirred for 24 hours under N2 to give a yellow mixture. Water was added and the aqueous layer was extracted with CHCl3. The combined extracts were washed with brine and dried over Na2SO4. After rotary evaporation, the resulting residue was purified by column chromatography on silica gel using Et2O:CH2Cl2 (3:1) as the eluent to give the title compound. (3.53 g, 74%). 1H NMR (CDCl3): δ 3.58 (s, 3H), 4.02-4.19 (m, 4H), 6.55 (s, 1H), 7.33-7.41 (m, 1H), 7.52-7.56 (m, 1H), 7.62-7.75 (m, 4H), 8.19 (d, J=1.7, 7.9 Hz, 1H); HRMS: Calcd. for C17H15N3O4 325.1062, found 325.1050.

Workup

  1. customresulting in an orange solution
  2. customwas syringed into the above mixture at room temperature under N2
  3. customto give a yellow mixture
  4. extractionthe aqueous layer was extracted with CHCl3
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter rotary evaporation
  8. customthe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2388688d3a9c4897afc29cbf5d4f07e2
Source dataset
uspto-grants-2002_04
Patent number
US06376664B1

Reaction notes

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