Sodium hydride → 4-Fluoro-2-(1,1-dioxo-1 lambda6-[1,2]thiazinan-2-yl)benzonitrile

HRID 28370

反応式

HRID 28370 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]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>CN(C=O)C.C1COCC1>[F:20][C:18]1[CH:19]=[CH:12][C:13]([C:14]#[N:15])=[C:16]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][S:2]2(=[O:8])=[O:1])[CH:17]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 775452,4-DifluorobenzonitrileHCID 3035081,4-Butanesultam

生成物 1

HCID 587773584-Fluoro-2-(1,1-dioxo-1 lambda6-[1,2]thiazinan-2-yl)benzonitrile収率 8.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,1-dioxo[1,2]thiazinane (8.84 g, 65.4 mmol) in DMF (20 mL) and THF (10 mL) was added portion-wise sodium hydride (1.65 g, 65.5 mmol, 95%). After stirring for 30 min, 2,4-difluorobenzonitrile (10.0 g, 72 mmol) was added and the mixture was stirred at 90° C. for 2.5 h. The mixture was cooled and concentrated and the residue was purified by flash chromatography eluting with 0%-10% EtOAc/hexane to give the title compound as white needles (1.37 g, 8% yield). 1H-NMR (500 MHz, CDCl3) δ: 7.70 (1H, dd, J=8.8, 5.8 Hz), 7.30 (1H, dd, J=8.8, 2.4 Hz), 7.15-7.12 (1H, m), 3.72 (2H, t, J=5.3 Hz), 3.33 (2H, t, J=6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS [M+H]+ calcd for C11H12N2FO2S: 255.06; found: 255.19.

後処理

  1. stirringthe mixture was stirred at 90° C. for 2.5 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography
  5. washeluting with 0%-10% EtOAc/hexane

出典と根拠

ORDレコード
ord-029848d6bf114264981eac0887db4854
出典データセット
uspto-grants-2008_09
特許番号
US07419969B2

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