2,4,6-Trimethylpyridine → HCID 15886700, compound

HRID 397002Notes

Reaction equation

HRID 397002 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.N1C(C)=CC(C)=CC=1C.[CH2:24]([S:31](Cl)(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.C(OCC)(=O)C>[CH2:24]([S:31]([NH:1][C:2]1[C:3](=[O:14])[N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 10035571Ethyl (3-amino-2-oxopyridin-1(2H)-yl)acetate

Product 1

HCID 15886700HCID 15886700, compoundYield 54,561.102%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of ethyl (3-amino-2-oxo-1,2-dihydropyridyl)acetate (40.0 g, 0.204 mole) and 2,4,6-collidine (54 mL, 0.408 mole) in tetrahydrofuran (200 mL) was cooled in an ice bath. A solution of benzylsulfonyl chloride (38.9 g, 0.204 mmole) in tetrahydrofuran (200 mL) was added over a 50-minute period. After addition was complete, the solution was stirred for 30 minutes at 0° C. The reaction mixture was diluted with ethyl acetate (1.2 L), washed with 1.0N HCl (until aqueous layer is pH 1), water (50 mL), saturated sodium bicarbonate (100 mL), and brine (2×50 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was recrystallized from chloroform. 39 g of the title compound was isolated. To the mother liquor was added silica gel. The solution was swirled, then filtered through a sintered glass funnel, washing with 50% ethyl acetate in dichloromethane. The solvent was removed from the filtrate, and the residue was recrystallized from chloroform. An additional 13 g of the title compound was isolated to afford a total of 52.00 g (75% yield) of the title compound as a tan solid. Rf=0.32 (silica gel, 20% ethyl acetate in dichloromethane). m.p. 48-49° C.

Workup

  1. additionAfter addition
  2. washwashed with 1.0N HCl (until aqueous layer is pH 1), water (50 mL), saturated sodium bicarbonate (100 mL), and brine (2×50 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customThe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-3c1d80ffd8fe417f8d3f61bf509d0540
Source dataset
uspto-grants-2003_08
Patent number
US06608204B1

Reaction notes

Loading…