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

HRID 581755노트

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HRID 581755 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aecb0f90c5244614b4bf6157041e96ed
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922711

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