Methanol → HCID 10926289, compound

HRID 1953134Notes

Reaction equation

HRID 1953134 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 was removed by filtration
  4. customthe methanol was evaporated
  5. customThe residue obtained
  6. extractionwas extracted with chloroform
  7. washthe chloroform was washed 3 times with water
  8. dry with materialdried over magnesium sulfate
  9. customAfter evaporation of the solvent
  10. customthe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-64f63e1b65d942b9a59fd2e240251a52
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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