Sodium Bicarbonate → 3-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamide

HRID 1800498Notes

Reaction equation

HRID 1800498 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([F:12])([F:11])[F:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([CH3:22])[CH3:21])#[N:19]>O1CCCC1>[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([F:10])([F:11])[F:12])=[C:6]([OH:8])[CH:7]=1)=[O:27])([CH3:22])[CH3:21])#[N:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 159190985-Amino-2-trifluoromethyl-phenolHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 684185013-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a two-layer solution of 5-amino-2-(trifluoromethyl)phenol (1.50 g, 8.46 mmol) in tetrahydrofuran (25 mL)/1N aqueous sodium hydrogen carbonate solution (25 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (15 mL), and the mixture was stirred at room temperature for 4 hr. The aqueous layer was separated, and extracted with ethyl acetate (200 mL). The combined organic layer was washed with saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with ethyl acetate/hexane to give the title compound (2.03 g, 69%) as a colorless powder.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe combined organic layer was washed with saturated brine (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was triturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a05746c99ea544f0adc5595ca957ff7a
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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