Dimethylformamide → 3-(Benzoxazol-2-yloxy)-1-butyl-4-methoxypyridine-2-thione

HRID 416566Notes

Reaction equation

HRID 416566 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8](C)=[C:7]([OH:12])[C:6]1=[S:13])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.CN([CH:29]=[O:30])C>>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[O:12][C:7]1[C:6](=[S:13])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[O:30][CH3:29]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 119862-ChlorobenzoxazoleHCID 24758Sodium hydrideHCID 222665331-Butyl-3-hydroxy-4-methylpyridine-2-thione

Product 1

HCID 222664813-(Benzoxazol-2-yloxy)-1-butyl-4-methoxypyridine-2-thioneYield 92%

Procedure

To a solution of 1-butyl-3-hydroxy-4-methylpyridine-2-thione (2-034-06) (50 mg) in DMF (1.0 mL) was added sodium hydride (60% wt, 15 mg) at room temperature. After the reaction mixture was stirred for 20 min, to the reaction mixture was added 2-chlorobenzoxazole (85 mg), and the reaction mixture was stirred at 75° C. for 17 h. After the reaction was quenched with water, the solvent was evaporated. To the residue were added aqueous saturated ammonium chloride solution and ethyl acetate, and the organic layer was separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The crude product was purified by column chromatography (toluene/acetone=4/1) to give 3-(benzoxazol-2-yloxy) -1-butyl-4-methoxypyridine-2-thione (2-034) (73 mg, 92%) as a yellow crystal. The obtained crystal was purified by recrystallization from methylene chloride and diethyl ether.

Workup

  1. customat room temperature
  2. stirringthe reaction mixture was stirred at 75° C. for 17 h
  3. customAfter the reaction was quenched with water
  4. customthe solvent was evaporated
  5. additionTo the residue were added aqueous saturated ammonium chloride solution and ethyl acetate
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted three times with ethyl acetate
  8. washThe combined organic layers were washed water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe crude product was purified by column chromatography (toluene/acetone=4/1)

Sources & evidence

ORD record
ord-de9f05be111149c5b7a7388fe125c597
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

Loading…