1,4-Dioxane → HCID 18919096, compound

HRID 1291208Notes

Reaction equation

HRID 1291208 reaction equation
O1CCOCC1.[C:7]([N:11]1[C:16](=[O:17])[C:15]([Cl:18])=[C:14](Cl)[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8].[Cl:20][C:21]1[CH:40]=[CH:39][C:24]([C:25]([C:27]2[CH:38]=[CH:37][C:30]([CH2:31][NH:32][CH2:33][CH2:34][CH2:35][OH:36])=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>O>[C:7]([N:11]1[C:16](=[O:17])[C:15]([Cl:18])=[C:14]([N:32]([CH2:33][CH2:34][CH2:35][OH:36])[CH2:31][C:30]2[CH:29]=[CH:28][C:27]([C:25](=[O:26])[C:24]3[CH:39]=[CH:40][C:21]([Cl:20])=[CH:22][CH:23]=3)=[CH:38][CH:37]=2)[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 18918916HCID 18918916, compound

Product 1

HCID 18919096HCID 18919096, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

In a solvent mixture of dioxane (5 ml) and water (5 ml) were dissolved 2-tert-butyl-4,5-dichloro-3(2H)-pyridazinone (473 mg) and 3-[4-(4-chlorobenzoyl)benzyl-amino]-1-propanol (1.30 g) and the mixture was stirred at 100° C. for 64 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=4:1-2:1) to provide the title compound as white powder (120 mg; yield 12%). 1H-NMR (CDCl3) δ: 1.63(9H,s), 1.83-1.98(3H,m), 3.51(2H,t,J=7.2Hz), 3.70(2H,m), 4.71(2H,m), 7.40(2H,d,J=8.4Hz), 7.46(2H,d,J=8.4Hz), 7.60(1H,s), 7.75(2H,d,J=8.4Hz), 7.77(2H,d,J=8.4Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-03d9822f5e6e4562b28c8aa2c545cd61
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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