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

HRID 250724ノート

反応式

HRID 250724 の反応式
[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

参加物

6

反応物 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

生成物 1

HCID 577580833-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide収率 70.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ea61d4d7423a41729e99a2e3da681c3a
出典データセット
uspto-grants-2011_01
特許番号
US07863310B2

反応ノート

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