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

HRID 1532010노트

반응식

HRID 1532010 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a 0.08 M 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 1 M 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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b50a4c3532b46a2b4adae01bd1e1d78
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200995B1

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