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

HRID 1821662

反応式

HRID 1821662 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-90620fe223434362948d5aa094bb8a12
出典データセット
uspto-grants-2009_10
特許番号
US07608563B2

関連ノート

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