Sodium Carbonate → 3-[3,6-dihydro-4-(3-methylphenyl)-1(2H)-pyridinyl]-6-(methylthio)pyridazine

HRID 359432Notes

Reaction equation

HRID 359432 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=1.Cl.[CH3:11][C:12]1[CH:13]=[C:14]([C:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:11][C:12]1[CH:13]=[C:14]([C:18]2[CH2:23][CH2:22][N:21]([C:2]3[N:3]=[N:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=3)[CH2:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2524753-Chloro-6-(methylthio)pyridazineHCID 190955564-(3-Methylphenyl)-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)

Product 1

HCID 151247413-[3,6-dihydro-4-(3-methylphenyl)-1(2H)-pyridinyl]-6-(methylthio)pyridazineYield 18%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.2 parts of 3-chloro-6-(methylthio)pyridazine, 3.14 parts of 1,2,3,6-tetrahydro-4-(3-methylphenyl)pyridine hydrochloride, 5.3 parts of sodium carbonate and 80 parts of 1-butanol was stirred for 48 hours at reflux temperature. The reaction mixture was evaporated. Water was added. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 0.8 parts (18%) of 3-[3.6-dihydro-4-(3-methylphenyl)-1(2H)-pyridinyl]-6-(methylthio)pyridazine; mp. 129.8° C. (compound 214).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionWater was added
  4. extractionThe product was extracted with trichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from 2-propanol
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-ac489307cb3f4b548ab89f65da832cc9
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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