Sodium hydride → HCID 68687791, compound

HRID 2238587Notes

Reaction equation

HRID 2238587 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:12]2[N:11]=[C:10]([CH3:13])[N:9]([CH3:14])[C:8]=2[CH:7]=[C:6]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=1.Cl[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:23][CH2:22][CH2:21]1>CN(C)C=O>[O:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]([O:3][C:4]2[C:12]3[N:11]=[C:10]([CH3:13])[N:9]([CH3:14])[C:8]=3[CH:7]=[C:6]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127921574-ChlorochromanHCID 68690597Methyl 4-hydroxy-1,2-dimethyl-1H-benzo[d]imidazole-6-carboxylate

Product 1

HCID 68687791HCID 68687791, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.71 g, 18 mmol) in N,N-dimethylformamide (40 mL) was added a suspension of methyl 4-hydroxy-1,2-dimethyl-1H-benzimidazole-6-carboxylate (3.0 g, 14 mmol, WO 2004054984) in N,N-dimethylformamide (40 mL) dropwise under nitrogen atmosphere at room temperature. After stirring for 20 minutes, a solution of 4-chlorochromane (4.6 g, 27 mmol, WO 2000078751) in N,N-dimethylformamide (10 mL) was added at room temperature. The reaction mixture was warmed to 70° C. for 2.5 hours, cooled to room temperature, and stirred for 18 hours at the same temperature. The reaction mixture was quenched with water and extracted with ethyl acetate (250 mL×2). The combined extracts were washed with sodium hydrogencarbonate aqueous solution, ammonium chloride aqueous solution and brine, dried over sodium sulfate, and concentrated in vacuum. The resulting solid was suspended with ethyl acetate and diethyl ether, and collected by filtration to give the title compound as a white solid (2.95 g, 61%):

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. stirringstirred for 18 hours at the same temperature
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate (250 mL×2)
  6. washThe combined extracts were washed with sodium hydrogencarbonate aqueous solution, ammonium chloride aqueous solution and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuum
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-44b5dfea0ee943f1b5927ea077e7d8d1
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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