Potassium Carbonate → 3-(4-Aminophenylthio)-6-phenylpyridazine

HRID 2395353Notes

Reaction equation

HRID 2395353 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[N:3]=[N:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 885153-Chloro-6-phenylpyridazine

Product 1

HCID 189716613-(4-Aminophenylthio)-6-phenylpyridazineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-6-phenylpyridazine (0.026 moles, 5.0 g), 4-aminothiophenol (0.026 moles, 3.3 g) and potassium carbonate (0.026 moles, 3.6 g) were stirred in 250 ml ethanol for 3 days. The reaction was filtered, concentrated, ethyl acetate added, washed with water and dried over sodium sulfate. The solution was concentrated and the product purified by HPLC over silica gel eluted with 50% ethyl acetate/hexane to yield 3-(4-aminophenylthio)-6-phenylpyridazine 6.0 g, 83%. Mass Spec (FD) 279. Calculated for C16H13N3S: C, 68.79; H, 4.69; N, 15.04. Found: C, 68.87; H, 4.43N, 15.31.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. additionethyl acetate added
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated
  7. customthe product purified by HPLC over silica gel
  8. washeluted with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9487680f56e2438ca245d473839cb7c7
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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