Triethylamine → 3-[4-(3-Methylphenyl)-1-piperazinyl]-6-(methylsulfonyl)pyridazine

HRID 359430

Reaction equation

HRID 359430 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([C:2]3[N:3]=[N:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=3)[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 831111-(m-Tolyl)piperazineHCID 2524763-Chloro-6-(methylsulfonyl)pyridazine

Product 1

HCID 151246013-[4-(3-Methylphenyl)-1-piperazinyl]-6-(methylsulfonyl)pyridazineYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.2 parts of 3-chloro-6-(methylsulfonyl)pyridazine, 3 parts of 1-(3-methylphenyl)piperazine, 2 parts of N,N-diethylethanamine and 180 parts of benzene was stirred for 24 hours at reflux. The reaction mixture was evaporated. Water was added to the residue. The precipitated product was filtered off, washed with water and dissolved in trichloromethane. The solution was dried, filtered and evaporated. The residue was crystallized from methanol. The product was filtered off and dried, yielding 5 parts (89%) of 3-[4-(3-methylphenyl)-1piperazinyl]-6-(methylsulfonyl)pyridazine; mp. 201° C. (compound 209).

Workup

  1. temperatureat reflux
  2. customThe reaction mixture was evaporated
  3. additionWater was added to the residue
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. dissolutiondissolved in trichloromethane
  7. customThe solution was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from methanol
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-a7e0dd8e74e54c38915d3c015f941e11
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Linked notes

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