2,4,6-Trimethylpyridine → HCID 15886700、化合物

HRID 2257099ノート

反応式

HRID 2257099 の反応式
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:7]1=[O:13])[CH3:2].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>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][S:31]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])[C:7]1=[O:13])[CH3:2]

参加物

6

反応物 3

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

生成物 1

HCID 15886700HCID 15886700、化合物収率 54,561.102%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e1268e3ac6f9423a99bcfb9338bee91b
出典データセット
uspto-grants-1997_08
特許番号
US05656645

反応ノート

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