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

HRID 52779Notes

Reaction equation

HRID 52779 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-724c12624b05432a932c9b3f8c67c733
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Reaction notes

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