Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide

HRID 250724노트

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HRID 250724 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].Cl.[CH3:15][NH:16][O:17][CH3:18].Cl.CN(C)CCCN=C=NCC.C(N(C1C=CC=CN=1)CC)C>ClCCl>[CH3:15][N:16]([O:17][CH3:18])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1

참가 물질

6

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2306533-Fluoro-4-nitrobenzoic acidHCID 232542N,N-Diethylpyridin-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 577580833-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide수율 70.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dissolve 3-Fluoro-4-nitro-benzoic acid (10.7 g, 57.71 mmol) in 1000 mL anhydrous dichloromethane. Add N,O-Dimethylhydroxylamine hydrochloride (4.5 g, 46.17 mmol), followed by 1-(3 dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (16.60 g, 86.57 mmol) and 4 diethylaminopyridine (6.77 g, 55.4 mmol). Stir at room temperature under nitrogen atmosphere overnight. Concentrate under reduced pressure and partition the residue between ethyl acetate (300 mL) and water (100 mL). Wash the organic layer with saturated aqueous sodium chloride (4×30 mL) and dry over magnesium sulfate. Concentrate under reduced pressure to provide the desired compound (7.4 g, 56%).

후처리

  1. concentrationConcentrate under reduced pressure
  2. custompartition the residue between ethyl acetate (300 mL) and water (100 mL)
  3. washWash the organic layer with saturated aqueous sodium chloride (4×30 mL)
  4. dry with materialdry over magnesium sulfate
  5. concentrationConcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-ea61d4d7423a41729e99a2e3da681c3a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863310B2

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