Sodium Bicarbonate → HCID 59596236, 화합물

HRID 2264770노트

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HRID 2264770 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2(C3C=CN=CC=3)[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:25][C:26]([S:29](N)=[O:30])([CH3:28])[CH3:27].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4](/[C:8](/[C:16]2[CH:15]=[C:14]([Cl:17])[CH:13]=[CH:12][C:11]=2[C:10]#[N:18])=[N:9]\[S:29]([C:26]([CH3:28])([CH3:27])[CH3:25])=[O:30])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 59596238HCID 59596238, 화합물

생성물 1

HCID 59596236HCID 59596236, 화합물수율 70.3%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

Titanium(IV) ethoxide (1M in tetrahydrofuran, 7.07 mL, 7.07 mmol) was added to 2-(3-bromobenzoyl)-4-chlorobenzonitrile (Scheme #18 R, 1.03 g, 3.21 mmol) at room temperature under argon atmosphere. 2-Methyl-2-propanesulfinamide (0.428 g, 3.53 mmol) was added 2 minutes later. The reaction mixture was refluxed overnight and then stirred at 50° C. for 24 h. The mixture was cooled to ambient temperature and diluted with methanol (7 mL). Saturated aqueous sodium bicarbonate was added and the mixture was diluted with ethyl acetate. The gelatinous precipitate formed was filtered off through a pad of magnesium sulfate (top) and diatomaceous earth (bottom). The filtrate was concentrated and the residue was purified by flash chromatography using ethyl acetate in heptane (0-40%) affording 0.956 g (70% yield) of the title compound. 1H NMR (DMSO-d6) δ 8.01 (d, J=6.53 Hz, 1 H), 7.95-7.75 (m, 3 H), 7.71 (s, 1 H), 7.52-7.44 (m, 2 H), 1.28 (s, 9 H).

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureThe mixture was cooled to ambient temperature
  3. customThe gelatinous precipitate formed
  4. filtrationwas filtered off through a pad of magnesium sulfate (top) and diatomaceous earth (bottom)
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-c70899d070d045fdbd0a688991b239f2
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855213B2

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