Sodium hydride → 2-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzonitrile

HRID 348146ノート

反応式

HRID 348146 の反応式
[O:1]=[S:2]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].F[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>CN(C)C=O.O>[O:1]=[S:2]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 3035081,4-Butanesultam

生成物 1

HCID 235683982-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzonitrile収率 70.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Added to a solution of 1,1-dioxo[1,2]thiazinane (3.37 g, 25 mmol) in dimethylformamide (35 mL) was sodium hydride (0.675 g, 25 mmol, 95%) and the mixture stirred at room temperature for 15 min. 2-Fluorobenzonitrile (3.37 mL, 31.3 mmol) was added and the mixture stirred at 80° C. for 18 h. The mixture was cooled, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, then dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (SiO2) eluting with 10%-100% ethyl acetate/hexane. The isolated solid was recrystallized from hot ethyl acetate/hexane (2:1) to give the title compound as white crystals (4.15 g, 70% yield). 1H-NMR (300 MHz, CDCl3) δ ppm: 7.70 (1H, dd, J=7.7, 1.1 Hz), 7.64–7.53 (2H, m), 7.41 (1H, td, J=7.3, 1.6 Hz), 3.72 (2H, t, J=5.5 Hz), 3.32 (2H, t, J=6.0 Hz), 2.40–2.32 (2H, m), 2.05–1.97 (2H, m). LCMS [M+H]+ calcd for C11H12N2O2S: 237.06; found: 237.10.

後処理

  1. stirringthe mixture stirred at 80° C. for 18 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2)
  8. washeluting with 10%-100% ethyl acetate/hexane
  9. customThe isolated solid was recrystallized from hot ethyl acetate/hexane (2:1)

出典と根拠

ORDレコード
ord-a77b738e422642fd9c2f6a9e77157cc3
出典データセット
uspto-grants-2007_02
特許番号
US07176196B2

反応ノート

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