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

HRID 52779ノート

反応式

HRID 52779 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-724c12624b05432a932c9b3f8c67c733
出典データセット
uspto-grants-1997_04
特許番号
US05616789

反応ノート

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