3-Amino-p-cresol → 3-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide

HRID 2190377Notes

Reaction equation

HRID 2190377 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].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>[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]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8])=[O:24])([CH3:19])[CH3:18])#[N:16]

Participants

5

Reactant 3

HCID 178203-Amino-p-cresolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 673120273-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a two-layer solution of 3-amino-4-methylphenol (3.25 g, 26.4 mmol) in tetrahydrofuran (20 mL)/1N aqueous sodium hydrogencarbonate solution (39 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 3 hr. The aqueous layer was separated, and extracted with ethyl acetate (100 mL). The combined organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate (45 mL)/hexane (45 mL) to give the title compound (5.95 g, 77%) as a colorless powder.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL)
  4. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was recrystallized from ethyl acetate (45 mL)/hexane (45 mL)

Sources & evidence

ORD record
ord-c9ce43a800974d84827718b2e3df1c3e
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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