Sodium Carbonate → 3-[4-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]-6-(methylthio)pyridazine

HRID 981649Notes

Reaction equation

HRID 981649 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=1.[O:10]1[CH2:14][CH2:13][N:12]=[C:11]1[C:15]1[CH:30]=[CH:29][C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[O:10]1[CH2:14][CH2:13][N:12]=[C:11]1[C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][N:26]([C:2]3[N:3]=[N:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=3)[CH2:27][CH2:28]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2524753-Chloro-6-(methylthio)pyridazineHCID 149891791-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]piperazine

Product 1

HCID 149893073-[4-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]-6-(methylthio)pyridazineYield 11.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.4 parts of 3-chloro-6-(methylthio)pyridazine, 4.5 parts of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]piperazine, 1.6 parts of sodium carbonate and 80 parts of 1-butanol was stirred for 5 days at reflux temperature. The reaction mixture was evaporated and the residue was dissolved in trichloromethane. The organic phase was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 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 0.7 parts (11.2%) of 3-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]-propyl]-1-piperazinyl]-6-(methylthio)pyridazine; mp. 163.1° C. (comp. 83).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in trichloromethane
  4. washThe organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97:3 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-f5783ceed5ef49cdaffd092a25269479
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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