Sodium Hydroxide → HCID 53870579, compound

HRID 1637644Notes

Reaction equation

HRID 1637644 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([SH:9])[N:4]=1.Cl[CH2:11][C:12]1[C:17]([CH3:18])=[C:16]([S:19][CH2:20][CH2:21][CH2:22][S:23][C:24]2[CH:25]=[CH:26][C:27]3[N:28]([C:30]([N+:33]([O-:35])=[O:34])=[CH:31][N:32]=3)[N:29]=2)[CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>CC(O)C>[CH3:18][C:17]1[C:12]([CH2:11][S:9][C:5]2[N:4]=[C:3]([CH3:2])[CH:8]=[CH:7][N:6]=2)=[N:13][CH:14]=[CH:15][C:16]=1[S:19][CH2:20][CH2:21][CH2:22][S:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([C:30]([N+:33]([O-:35])=[O:34])=[CH:31][N:32]=2)[N:29]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 53870579HCID 53870579, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 4-methyl-pyrimidine-2-thiol hydrochloride (0.46 g, 2.8 mmol) and 6-[3-(2-chloromethyl-3-methyl-pyridin-4-ylsulfanyl)-propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine (1.03 g, 2.5 mmol) in 2-propanol (50 ml) is heated under reflux for 4 h under a nitrogen atmosphere. After cooling, the mixture is treated with ice water (100 ml), adjusted to pH 10 with 40% strength sodium hydroxide solution, and extracted with ethyl acetate. The combined extracts are washed with sodium carbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue is chromatographed (silica, toluene/dioxane 2:1) and crystallized from acetonitrile to give the title compound as a colourless solid, 0.49 g (39%). M.p. 136-8° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 h under a nitrogen atmosphere
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts are washed with sodium carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue is chromatographed (silica, toluene/dioxane 2:1)
  9. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-b75ef14d22d84e5fb97083b1883e6b0a
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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