Water → HCID 15937178, compound

HRID 522373Notes

Reaction equation

HRID 522373 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].O.[C:10](=O)(O)[O-:11].[Na+].C(C(C(Cl)=O)C(Cl)=O)C.[C:24]([O:27][CH2:28][CH3:29])(=[O:26])[CH3:25]>>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:11])[CH2:25][C:24]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 95842-FluoroanilineHCID 516892Sodium BicarbonateHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 15937178HCID 15937178, compound

Procedure

To a solution of 2-fluoroaniline (8.67 ml) in ethyl acetate (266 ml) was added water (200 ml) and sodium bicarbonate (15.12 g). Ethyl malonyl chloride (13.82 ml) was added and the solution was stirred at room temperature for 1 hour. The two layers were separated and the organic phase was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over sodium sulfate and evaporated to provide a brownish oil. The crude reaction mixture was used directly in the next step. LRMS (ES+) m/z 226.1 (M+H)+.

Workup

  1. customThe two layers were separated
  2. washthe organic phase was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto provide a brownish oil
  6. customThe crude reaction mixture

Sources & evidence

ORD record
ord-65a8fc9c63d54095b09dcaf6c02f09ed
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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