2,6-Lutidine → HCID 19436791, compound

HRID 1735002Notes

Reaction equation

HRID 1735002 reaction equation
[Cl:1][C:2]1[C:3]([OH:10])=[N:4][N:5]([CH3:9])[C:6]=1[S:7][CH3:8].Cl[C:12]1[N:13]=[N:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1.N1C(C)=CC=CC=1C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:10][C:12]2[N:13]=[N:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)=[N:4][N:5]([CH3:9])[C:6]=1[S:7][CH3:8]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 109756123-Chloro-5-methoxypyridazineHCID 178503286HCID 178503286, compound

Product 1

HCID 19436791HCID 19436791, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-ol which is a known compound (2.7 g, 0.015 mole), 3-chloro-5-methoxypyridazine (1.45 g, 0.01 mole), and 2,6-lutidine (1.4 mL, 0.012 moles) were heated to reflux in toluene (40 mL) under N2 for 18 h. The mixture was then poured into aqueous ammonium chloride and extracted 3×100 mL with ethyl acetate. The organic layers were washed with water and brine, dried (MgSO4), filtered and evaporated in vacuo. The crude solid was purified by flash chromatography to give 3-[[4-chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-yl]oxy]-5-methoxypyridazine (1.1 g, 26% yield) as a white solid.

Workup

  1. temperaturewere heated
  2. extractionextracted 3×100 mL with ethyl acetate
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude solid was purified by flash chromatography

Sources & evidence

ORD record
ord-291556504ef34a56bbe083998be37db7
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

Loading…