Potassium Carbonate → N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide

HRID 1167663Notes

Reaction equation

HRID 1167663 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1F.[Cl:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[N:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:27][C:23]1[CH:22]=[C:21]([Cl:20])[CH:26]=[N:25][CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5823053-Hydroxy-5-chloropyridineHCID 43377386N-(2-furanylmethyl)2-fluoro-5-nitrobenzamide

Product 1

HCID 54136240N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamideYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a 0.08M solution of N-(2-furanylmethyl) 2-fluoro-5-nitrobenzamide (2.64 g, 10 mmol, from Example 35.1) in anhydrous DMSO was added 5-chloro-3-pyridinol (1.36 g, 10.5 mmol, Acros) followed by K2CO3 (1.38 g, 10 mmol). The resulting mixture was stirred at ambient temperature for 1 hr. The crude reaction mixture was diluted with a 1M solution of aqueous hydrochloric acid (125 mL) and extracted 3× with EtOAc (125 mL). The organic layers were combined and washed twice with brine (200 mL), dried over Na2SO4, and concentrated under vacuum to yield 3.7 g (100%) of N-(2-furanylmethyl) 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide as a pale yellow foam which was used without further purification.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted 3× with EtOAc (125 mL)
  3. washwashed twice with brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6aff2c59d7e542a89f544c3b03546e64
Source dataset
uspto-grants-2003_09
Patent number
US06620827B2

Reaction notes

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