Water → 6-Chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide

HRID 1821662

반응식

HRID 1821662 반응식
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].CC(C)([O-])C.[K+].Cl[C:17]1[N:18]=[N+:19]([O-:24])[C:20]([Cl:23])=[CH:21][CH:22]=1.O>O1CCOCC1.CS(C)=O>[Cl:23][C:20]1[N+:19]([O-:24])=[N:18][C:17]([O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[S:2][CH3:1])=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 61261o-(Methylthio)phenolHCID 2609103,6-Dichloropyridazine 1-oxideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 229399336-Chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide수율 56.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 312751,4-Dioxane용매

실험 절차

In a mixed solvent of 1,4-dioxane (5 mL) and dimethylsulfoxide (5 mL) was dissolved 454 mg (3.24 mmol) of 2-(methylsulfanyl)phenol, to the solution was added 519 mg (4.63 mmol) of potassium tert-butoxide and the mixture was stirred for 35 minutes. To the mixture was added 424 mg (2.57 mmol) of 3,6-dichloropyridazine 1-oxide and the resulting mixture was stirred for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel chromatography (Wakogel C-100, eluted with hexane:ethyl acetate=3:1) to obtain 391 mg (1.46 mmol, Yield: 56.8%) of 6-chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide.

후처리

  1. stirringthe resulting mixture was stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe obtained residue was purified by silica gel chromatography (Wakogel C-100, eluted with hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-90620fe223434362948d5aa094bb8a12
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608563B2

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