Ethyl Acetate → HCID 59516907, compound

HRID 1698617Notes

Reaction equation

HRID 1698617 reaction equation
F[B-](F)(F)F.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=2[F:29])[C:16]([NH2:18])=[S:17])=[CH:10][CH:9]=1)#[N:7].[C:30](OCC)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:30][S:17][C:16](=[NH:18])[CH:15]([NH:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:13][CH:12]=1)[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=1[F:29]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 26255TetrafluoroborateHCID 516892Sodium BicarbonateHCID 59517201HCID 59517201, compound

Product 1

HCID 59516907HCID 59516907, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 0.904 g of Me3O+BF4− to a solution of 2.01 g of 2-(4-cyanophenylamino)-2-(2-fluoro-3,5-dimethoxyphenyl)thioacetamide in 150 ml of acetonitrile under a nitrogen atmosphere, the mixture was stirred at room temperature for 5 hours. Next, 400 ml of ethyl acetate and 300 ml of saturated aqueous sodium hydrogencarbonate were added and the organic layer was washed with 300 ml of water and 300 ml of saturated brine. The mixture was dried over anhydrous magnesium sulfate and the desiccating agent was filtered off. The filtrate was concentrated under reduced pressure to give the title compound (2.05 g) as a light yellow solid.

Workup

  1. washthe organic layer was washed with 300 ml of water and 300 ml of saturated brine
  2. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccating agent was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a740da605afa494996c1f275aec9271a
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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