5-Amino-2-methylphenol → 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide

HRID 2190435Notes

Reaction equation

HRID 2190435 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].[C:15]([C:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([CH3:19])[CH3:18])#[N:16]>O1CCCC1.O>[C:15]([C:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1)=[O:24])([CH3:19])[CH3:18])#[N:16]

Participants

6

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 673134703-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamideYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-amino-2-methylphenol (3.00 g, 24.3 mmol) in tetrahydrofuran (20 mL) was added a suspension of sodium hydrogencarbonate (3.00 g, 36.5 mmol) in water (30 mL), and the mixture was vigorously stirred at room temperature. To this mixture was added dropwise a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride produced above in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. The aqueous layer was separated from the reaction mixture, and the organic layer was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and decolorized with activated carbon. The insoluble material was passed through a pad filled with two layers of silica gel and celite for filtration. The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate-hexane mixture to give the title compound (6.75 g, 94%) as a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. customThe aqueous layer was separated from the reaction mixture
  4. additionthe organic layer was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. additionfilled with two layers of silica gel and celite for filtration
  8. customThe solvent was evaporated under reduced pressure
  9. washthe obtained solid was washed with ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-85471b6a51e447f5845381f3204a5822
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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