Sodium Hydroxide → HCID 18799442, compound

HRID 1637643Notes

Reaction equation

HRID 1637643 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([SH:9])[N:3]=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>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH2:11][C:12]2[C:17]([CH3:18])=[C:16]([S:19][CH2:20][CH2:21][CH2:22][S:23][C:24]3[CH:25]=[CH:26][C:27]4[N:28]([C:30]([N+:33]([O-:35])=[O:34])=[CH:31][N:32]=4)[N:29]=3)[CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 18799442HCID 18799442, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 4,6-dimethyl-pyrimidine-2-thiol (0.35 g, 2.5 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 crystallized from acetonitrile to give the title compound as a colourless solid, 0.93 g (76%). M.p. 145-7° 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 crystallized from acetonitrile

Sources & evidence

ORD record
ord-2e431824a3df45938ef292aca7d3ea84
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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