Sodium Carbonate → HCID 23568418, 화합물

HRID 1822713

반응식

HRID 1822713 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 23568418HCID 23568418, 화합물수율 83%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 19096565Water ethanol용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cc84117856af40ea8ec7724d1735e0ae
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037908B2

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