Sodium Bicarbonate → 3-(1-cyano-1-methylethyl)-N-(4-ethyl-3-hydroxyphenyl)benzamide

HRID 1800469Notes

Reaction equation

HRID 1800469 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][CH3:11])=[C:7]([OH:9])[CH:8]=1.C(=O)([O-])O.[Na+].[C:17]([C:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])([CH3:21])[CH3:20])#[N:18]>O1CCCC1>[C:17]([C:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][CH3:11])=[C:7]([OH:9])[CH:8]=1)=[O:26])([CH3:21])[CH3:20])#[N:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 684194645-Amino-2-ethylphenol hydrochlorideHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 684191923-(1-cyano-1-methylethyl)-N-(4-ethyl-3-hydroxyphenyl)benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a two-layer solution of 5-amino-2-ethylphenol hydrochloride (2.2 g, 12.6 mmol) in tetrahydrofuran (20 mL)/1N aqueous sodium hydrogen carbonate solution (38 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 12 hr. The aqueous layer was separated, and extracted with ethyl acetate (80 mL). The combined organic layer was washed with water (40 mL) and saturated brine (40 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate (45 mL)/hexane (25 mL) was added to the obtained residue, and the obtained solid was collected by filtration to give the title compound (3.48 g, 90%) as a colorless powder.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (80 mL)
  3. washThe combined organic layer was washed with water (40 mL) and saturated brine (40 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. additionEthyl acetate (45 mL)/hexane (25 mL) was added to the obtained residue
  8. filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-48d3a63df8e748f48114d819959a3b06
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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