Sodium Hydroxide → HCID 67312828, compound

HRID 2190477Notes

Reaction equation

HRID 2190477 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][C:24]=1[O:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[Cl:1][C:2]1[C:10]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[C:24]([O:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)[CH:25]=1)=[O:6]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 668102752-Chloro-3-(1-cyano-1-methylethyl)benzoic acidHCID 67312965HCID 67312965, compound

Product 1

HCID 67312828HCID 67312828, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-3-(1-cyano-1-methylethyl)benzoic acid (1.98 g, 8.85 mmol) produced in Example A41(ii) in tetrahydrofuran (40 mL) were added oxalyl chloride (1.41 g, 11.1 mmol) and N,N-dimethylformamide (10 μL), and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in N,N-dimethylacetamide (40 mL). 4-Fluoro-3-(4-nitrophenoxy)aniline (4.69 g, 20.4 mmol) was added, and the mixture was stirred at room temperature for 14 hr. To the reaction mixture were added water (100 ml), 1N aqueous sodium hydroxide solution (50 mL) and ethyl acetate (200 mL). The organic layer was separated, washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give 2-chloro-3-(1-cyano-1-methylethyl)-N-[4-fluoro-3-(4-nitrophenoxy)phenyl]benzamide (2.01 g, 99%). The obtained compound was used in the next reaction without a further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in N,N-dimethylacetamide (40 mL)
  3. stirringthe mixture was stirred at room temperature for 14 hr
  4. customThe organic layer was separated
  5. washwashed with saturated brine (10 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0ae00c39a3f442a9859edc602e948f7
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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