Sodium methanethiolate → 4-Methoxy-3-(methylthio)-6-[3-(trifluoromethyl)phenyl]pyridazine

HRID 54655노트

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HRID 54655 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9].[CH3:20][S-:21].[Na+]>C1COCC1>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[N:3][C:2]=1[S:21][CH3:20]

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 199596893-Chloro-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine

생성물 1

HCID 199596674-Methoxy-3-(methylthio)-6-[3-(trifluoromethyl)phenyl]pyridazine수율 88.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Chloro-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine (2.0 g, 0.0069 mole, Compound No. 48) and sodium thiomethoxide (0.5 g, 0.0069 mole) were refluxed overnight under N2 in THF (50 mL). After this time no starting material was present by TLC. The mixture was partitioned between EtOAc-water. The aqueous layer was extracted again with EtOAc. The EtOAc layers were combined, washed with brine, dried (MgSO4), filtered and evaporated to give a crude oil. The oil was chromatographed on a Prep-500 using EtOAc-cyclohexane (3:17) to give 4-methoxy-3-(methylthio)-6-[3-(trifluoromethyl)phenyl]pyridazine (1.83 g, 88% yield, Compound No. 64) as a white solid.

후처리

  1. customThe mixture was partitioned between EtOAc-water
  2. extractionThe aqueous layer was extracted again with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude oil
  8. customThe oil was chromatographed on a Prep-500 using EtOAc-cyclohexane (3:17)

출처 및 근거

ORD 기록
ord-4892165b741043b8a4528e20cb38e091
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623072

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