Sodium Carbonate → HCID 23568418、化合物

HRID 1822713

反応式

HRID 1822713 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[C:5]#[N:6].Cl.[CH3:14][NH:15][OH:16].C(=O)([O-])[O-].[Na+].[Na+].[C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])#[C:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(OCC)(=O)C.O.C(O)C>[CH2:33]([O:32][C:30]([C:23]1([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:16][N:15]([CH3:14])[C:5]([C:4]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][C:3]=2[O:2][CH3:1])=[N:6]1)=[O:31])[CH3:34]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 69803Diethyl acetylenedicarboxylateHCID 77906N-methylhydroxylamine hydrochlorideHCID 856482,6-Dimethoxybenzonitrile

生成物 1

HCID 23568418HCID 23568418、化合物収率 83%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 19096565Water ethanol溶媒

反応条件

温度
80 °C

実験手順

To a stirred suspension of 2,6-dimethoxy-benzonitrile (0.82 g, 5 mmol) and N-methylhydroxylamine hydrochloride (1.66 g, 20 mmol) in 1:1 water/ethanol (20 mL) was added sodium carbonate (1.05 g, 10 mmol) in small portions and the resulting mixture stirred at 80° C. for 24 h. The reaction mixture was concentrated and the residue was re-dissolved into 1:1 water:ethanol (25 mL). To this solution was added diethyl acetylenedicarboxylate (0.96 mL, 6 mmol) and the resulting mixture stirred for 30 min at room temperature. The reaction mixture was then taken up in ethyl acetate (100 mL), washed successively with water and brine (50 mL each), dried (Na2SO4), filtered and concentrated to give a yellow oil. The crude product was purified on silica gel column (3:7 to 1:1 ethyl acetate/hexanes) to afford the title compound as a viscous yellow (1.5795 g, 83% yield). 1HNMR (500 MHz, CDCl3) δ: 7.32 (1H, t, J=8.24 Hz), 6.55 (2H, d, J=8.24 Hz), 4.38–4.24 (2H, m), 4.20–4.14 (2H, m), 3.80 (6H, s), 3.48 (1H, d, J=16.48 Hz), 3.03 (1H, d, J=16.48 Hz), 3.02 (3H, s), 1.33 (3H, t, J=7.02 Hz), 1.26 (3H, 7.02 Hz). HRMS (ESI) calcd for C18H25N2O7S (M+H): 381.1662; found: 381.1656.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was re-dissolved into 1:1 water
  3. stirringthe resulting mixture stirred for 30 min at room temperature
  4. washwashed successively with water and brine (50 mL each)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThe crude product was purified on silica gel column (3:7 to 1:1 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-cc84117856af40ea8ec7724d1735e0ae
出典データセット
uspto-grants-2006_05
特許番号
US07037908B2

関連ノート

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