Benzyl Alcohol → 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide

HRID 2114177노트

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HRID 2114177 반응식
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18]>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamide

생성물 1

HCID 231302675-benzyloxy-N,N-dimethyl-2-nitrobenzamide수율 89.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

Sodium hydride (210 mg) was suspended in DMF (10 mL), and the suspension was cooled to 0° C. and thereto were added benzyl alcohol (568 mg) and a solution of 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.00 g) in DMF (2 mL). The mixture was stirred at 50° C. for 0.5 hour and then concentrated. The residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3) to give 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide (1.18 g)

후처리

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3)

출처 및 근거

ORD 기록
ord-fc65824a0cfa40f8a7587440764e6c86
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432392B2

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