Sodium hydride → HCID 64005706、化合物

HRID 1776214ノート

反応式

HRID 1776214 の反応式
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[NH:3][CH2:2]1.[H-].[Na+].Cl[C:11]([CH3:15])([CH3:14])[C:12]#[CH:13]>CN(C)C=O>[CH3:14][C:11]([N:3]1[CH2:2][CH2:1][CH2:7][S:4]1(=[O:6])=[O:5])([C:12]#[CH:13])[CH3:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 6421571,3-Propanesultam

生成物 1

HCID 64005706HCID 64005706、化合物収率 44%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1,3-propanesultam (2.000 g, 16.5 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added 60% sodium hydride in mineral oil (1.981 g, 49.5 mmol) and the mixture was stirred at 0° C. for 1 hr. 3-Chloro-3-methyl-1-butyne (2.300 g, 22.4 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hr and then slowly warmed to room temperature and stirred for 16 hrs. The reaction was carefully quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography (0-70% ethyl acetate/hexanes) to afford the desired product as a yellow oil (1.35 g, 44%). 1H NMR (300 MHz, CDCl3) δ 3.52 (t, 2H, J=6.6 Hz), 3.23 (t, 2H, J=7.5 Hz), 2.46 (s, 1H), 2.42-2.28 (m, 2H), 1.74 (s, 6H).

後処理

  1. stirringthe reaction mixture was stirred at 0° C. for 1 hr
  2. temperatureslowly warmed to room temperature
  3. stirringstirred for 16 hrs
  4. customThe reaction was carefully quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried (anhydrous sodium sulfate)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (0-70% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-011a53df4f2b458a827379c2560733dd
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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