Sodium Bicarbonate → HCID 59596236、化合物

HRID 2264770ノート

反応式

HRID 2264770 の反応式
[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

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 59596238HCID 59596238、化合物

生成物 1

HCID 59596236HCID 59596236、化合物収率 70.3%

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c70899d070d045fdbd0a688991b239f2
出典データセット
uspto-grants-2010_12
特許番号
US07855213B2

反応ノート

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