Ethanol → 3-Ethoxy-4-nitrobenzamide

HRID 450526노트

반응식

HRID 450526 반응식
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].F[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([NH2:12])=[O:11]>C1COCC1>[CH2:1]([O:3][C:14]1[CH:13]=[C:9]([CH:8]=[CH:7][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([NH2:12])=[O:11])[CH3:2]

참가 물질

5

반응물 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 114239673-Fluoro-4-nitrobenzamide

생성물 1

HCID 672173043-Ethoxy-4-nitrobenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Ethanol (0.8 mL, 13.8 mmol) was added drop wise to a stirred suspension of sodium hydride (60% dispersion in oil, 0.550 g, 13.8 mmol) in anhydrous THF (15 mL) at 0° C. and the resulting solution stirred for 0.5 hours. To this solution was added 3-fluoro-4-nitrobenzamide (2.11 g, 11.5 mmol) drop wise in anhydrous THF (15 mL). After complete addition the solution was stirred at 0° C. for 0.5 hours, before being allowed to warm to ambient temperature. The reaction was stirred at ambient temperature for 18 hours, quenched with water (30 mL) and the aqueous layer extracted with DCM (3×50 mL). The organic layers were combined, washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The title compound was obtained as a yellow solid (1.694 g, 70% yield) after recrystallisation from MeOH.

후처리

  1. additionAfter complete addition the solution
  2. stirringwas stirred at 0° C. for 0.5 hours
  3. stirringThe reaction was stirred at ambient temperature for 18 hours
  4. customquenched with water (30 mL)
  5. extractionthe aqueous layer extracted with DCM (3×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7ae089f3185d40aaae29e2010e7bcc60
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486953B2

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