Hydrochloric Acid → HCID 178496276, 화합물

HRID 1407098

반응식

HRID 1407098 반응식
[N:1]([O-])=O.[Na+].[F:5][CH:6]([F:15])[O:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].Cl.[CH3:17][O:18][CH2:19][C:20](=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].CC([O-])=O.[Na+]>O.CO>[F:5][CH:6]([F:15])[O:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][N:1]=[C:21]([C:20](=[O:26])[CH2:19][O:18][CH3:17])[C:22]([O:24][CH3:25])=[O:23]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 9346202-(Difluoromethoxy)anilineHCID 23668193Sodium Nitrite

생성물 1

HCID 178496276HCID 178496276, 화합물수율 96%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

A solution of NaNO2 (2.378 g, 34.5 mmol) in H2O (10 mL) was added dropwise at 0° C. to a solution of 2-(difluoromethoxy)aniline. (3.59 mL, 28.7 mmol) in 6 M HCl aqueous solution (28.7 mL, 172 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (3.72 mL, 28.7 mmol) and NaOAc (14.14 g, 172 mmol) in MeOH (50 mL) pre-cooled at 0° C. The precipitate was collected by filtration, washed with water, and dissolved in AcOEt. The organic solution was washed with water, saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was washed with hexane/AcOEt (3/1) to give the title compound (8.70 g, 96% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.51 (3H, s), 3.89 (3H×0.5, s), 3.94 (3H×0.5, s), 4.68 (1H×0.5, s), 4.70 (1H×0.5, s), 6.63 (1H×0.5, t, J=72.7 Hz), 6.66 (1H×0.5, t, J=72.3 Hz), 7.10-7.34 (4H, m), 7.67 (1H×0.5, dd, J=8.3, 1.5 Hz), 7.90 (1H×0.5, dd, J=8.3, 1.5 Hz), 13.14 (1H×0.5, s), 14.96 (1H×0.5, br s).

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutiondissolved in AcOEt
  4. washThe organic solution was washed with water, saturated NaHCO3 aqueous solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane/AcOEt (3/1)

출처 및 근거

ORD 기록
ord-70700b4477844ceb95d9c93bb5768421
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916566B2

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