Sodium Bicarbonate → HCID 59596236, compound

HRID 2264770Notes

Reaction equation

HRID 2264770 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 59596236HCID 59596236, compoundYield 70.3%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c70899d070d045fdbd0a688991b239f2
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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