Methyl iodide → N-Methyl-3-nitro-N-(3-pyridinylmethyl)benzamide

HRID 726283ノート

反応式

HRID 726283 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([O-:3])=[O:2].[CH3:20]C(C)([O-])C.[K+].IC.C(=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[C:7]([N:9]([CH3:20])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([O-:3])=[O:2]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 7434213-Nitro-N-(3-pyridinylmethyl)benzamideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 22113238N-Methyl-3-nitro-N-(3-pyridinylmethyl)benzamide収率 85.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-nitro-N-(3-pyridylmethyl)benzamide (2.00 g) in tetrahydrofuran (40 ml) was added potassium tert-butoxide (917 mg) in one portion in an ice-cooled bath. The stirring was continued for 40 minutes and then iodomethane (0.53 ml) was added thereto. The reaction mixture was stirred at 0° C. for one hour, then at ambient temperature for five hours. Saturated sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. After dried over anhydrous magnesium sulfate and filtered, the solvent was removed in vacuo and the residue was purified by flash chromatography (methanol-chloroform 3%, V/V) to afford 3-nitro-N-methyl-N-(3-pyridylmethyl)benzamide (1.8 g) as a yellow oil.

後処理

  1. temperaturecooled bath
  2. waitat ambient temperature for five hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialAfter dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography (methanol-chloroform 3%, V/V)

出典と根拠

ORDレコード
ord-860d52d0baed48c8bd1793d53b3bbe22
出典データセット
uspto-grants-1998_01
特許番号
US05708173

反応ノート

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