Water → 6-Chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxide

HRID 2424283

반응식

HRID 2424283 반응식
CC(C)([O-])C.[K+].Cl[C:8]1[N:9]=[N+:10]([O-:15])[C:11]([Cl:14])=[CH:12][CH:13]=1.O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[OH:26]>O1CCOCC1.CS(C)=O>[Cl:14][C:11]1[N+:10]([O-:15])=[N:9][C:8]([O:26][C:20]2[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:19]=2[O:18][CH3:17])=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 145192-Methoxy-5-methylphenolHCID 2609103,6-Dichloropyridazine 1-oxideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 229400166-Chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxide수율 70.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 312751,4-Dioxane용매

실험 절차

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL) was dissolved 167.5 mg (1.21 mmol) of commercially available 2-methoxy-5-methylphenol, and 142.8 mg (1.27 mmol) of potassium tert-butoxide was added to the solution, then 202.9 mg (1.23 mmol) of 3,6-dichloropyridazine 1-oxide was added to the mixture and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 3 plates were used, developed by ethyl acetate:hexane=2:1) to obtain 226.5 mg (0.849 mmol, Yield: 70.2%) of 6-chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxide.

후처리

  1. additionwas added to the solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 3 plates were used, developed by ethyl acetate:hexane=2:1)

출처 및 근거

ORD 기록
ord-40362655c2a14723ad6a57f03b38de65
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964531B2

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