Dimethylformamide → HCID 22266539, compound

HRID 416567Notes

Reaction equation

HRID 416567 reaction equation
[CH2:1]([N:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([OH:12])[C:6]1=[S:13])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH3:16][N:17]([CH:19]=[O:20])C>>[O:20]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:16]=2[N:17]=[C:19]1[O:12][C:7]1[C:6](=[S:13])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:10]=[C:9]([CH3:11])[CH:8]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22266468HCID 22266468, compound

Product 1

HCID 22266539HCID 22266539, compoundYield 73%

Procedure

To a solution of 1-butyl-3-hydroxy-5-methylpyridine-2-thione (2-035-05) (300 mg) in DMF (6.0 mL) was added sodium hydride (60% wt, 79 mg) at room temperature. After the reaction mixture was stirred for 20 min, to the reaction mixture was added 2-chlorobanzoxazole (432 mg), and the reaction mixture was stirred at room temperature for 2 h. After the reaction was quenched with water, the solvent was removed. 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 with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (toluene/acetone=4/1) to give 3-(benzoxazol-2-yloxy)-1-butyl-4-methylpyridine-2-thione (2-035) 372 mg, 73%) as a yellow crystal. The obtained crystal was purified by recrystallization from methylene chloride and diethyl ether.

Workup

  1. customat room temperature
  2. additionwas added 2-chlorobanzoxazole (432 mg)
  3. stirringthe reaction mixture was stirred at room temperature for 2 h
  4. customAfter the reaction was quenched with water
  5. customthe solvent was removed
  6. additionTo the residue were added aqueous saturated ammonium chloride solution and ethyl acetate
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted three times with ethyl acetate
  9. washThe combined organic layers were washed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe crude product was purified by silica gel column chromatography (toluene/acetone=4/1)

Sources & evidence

ORD record
ord-a2764e5c2a0c4e9aa98cd7b2b7009f59
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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