Methanol → HCID 10926289, compound

HRID 2289587Notes

Reaction equation

HRID 2289587 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CO.Br[CH:16]([C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=1)[C:17]#[N:18]>[OH-].[Na+]>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([S:1][CH:16]([C:19]3[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=3)[C:17]#[N:18])[NH:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11747189HCID 11747189, compoundHCID 178488032HCID 178488032, compound

Product 1

HCID 10926289HCID 10926289, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-mercapto-5-methoxybenzimidazole (15.1 g, 0.14 mole) dissolved in 40 ml of 8.4% sodium hydroxide, was added 170 ml of methanol, followed by bromo(4-methoxy-3,5-dimethyl-2-pyridyl)acetonitrile (21.4 g, 0.11 mole) at room temperature. The mixture was heated to reflux for 1 h under a nitrogen atmosphere. The-resulting precipitate was removed by filtration and the methanol was evaporated. The residue obtained was extracted with chloroform, and the chloroform was washed 3 times with water and dried over magnesium sulfate. After evaporation of the solvent, the crude product was recrystallized from diethyl ether to give 22.6 g (90%) of the title compound as yellowish crystals: mp 193-197° C.; 1H NMR (CDCl3) δ 8.25 (s,1H), 7.65 (dd, 1H), 7.30 (m, 1H), 6.90 (m, 1H), 6.30 (br s, 2H), 3.95 (s, 3H), 3.75 (s, 3H), 2.50 (s, 3H), 2.20 (s, 3H) ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h under a nitrogen atmosphere
  3. customThe-resulting precipitate
  4. customwas removed by filtration
  5. customthe methanol was evaporated
  6. customThe residue obtained
  7. extractionwas extracted with chloroform
  8. washthe chloroform was washed 3 times with water
  9. dry with materialdried over magnesium sulfate
  10. customAfter evaporation of the solvent
  11. customthe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-56fa5f1c69264485b47758838fa2c1ab
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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