5-Amino-2-chlorophenol → N-(4-chloro-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide

HRID 1800511Notes

Reaction equation

HRID 1800511 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl: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>[Cl:9][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([C:17]([C:15]#[N:16])([CH3:18])[CH3:19])[CH:21]=2)=[CH:7][C:6]=1[OH:8]

Participants

5

Reactant 3

HCID 806765-Amino-2-chlorophenolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 68418799N-(4-chloro-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a two-layer solution of 5-amino-2-chlorophenol (3.19 g, 22.2 mmol) in tetrahydrofuran (50 mL)/1N aqueous sodium hydrogen carbonate solution (66 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (16 mL), and the mixture was stirred at room temperature for 6 hr. The aqueous layer was separated, and extracted with ethyl acetate (66 mL). The combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was triturated with ethyl acetate/hexane to give the title compound (6.65 g, 95%) as a colorless powder.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (66 mL)
  3. washThe combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 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-42006f588ccb435ba868e232d8beb213
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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