Isopropanol → 4-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide

HRID 536040ノート

反応式

HRID 536040 の反応式
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].F[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20].CCOC(C)=O>O>[CH3:18][NH:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:6][CH:3]([CH3:5])[CH3:4])=[C:9]([N+:19]([O-:21])=[O:20])[CH:10]=1)(=[O:16])=[O:15]

参加物

6

反応物 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 84680854-fluoro-N-methyl-3-nitrobenzenesulfonamide

生成物 1

HCID 699352384-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide収率 58%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

NaH (0.440 g, 11 mmol) was added to 20 mL of isopropanol and the resulting mixture stirred at room temperature. After 30 minutes, 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (2.34 g, 10 mmol) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was poured into EtOAc and water. The organic phase was separated, dried over Na2SO4, and concentrated in vacuo to give the crude product. Purification via column chromatography (1:1 petroleum ether/ethyl acetate) afforded N-methyl-4-[(1-methylethyl)oxy]-3-nitrobenzenesulfonamide (1.6 g, 58% yield) as a yellow solid. MS (m/z) 274.7 (M+H+)

後処理

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification via column chromatography (1:1 petroleum ether/ethyl acetate)

出典と根拠

ORDレコード
ord-16445e4b802040e1b77f22b45efca9d6
出典データセット
uspto-grants-2014_10
特許番号
US08859571B2

反応ノート

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