Dimethyl Sulfate → 5,6-bis(4-methoxyphenyl)-2-[4-(dimethylamino)benzyl]-2H-pyridazin-3-one

HRID 1699773Notes

Reaction equation

HRID 1699773 reaction equation
NC1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:9]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[N:8]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].S(OC)(OC)(=O)=O.CC(C)=O.[CH3:48][N:49]([CH3:52])[CH:50]=O>CC(C)=O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:10]2[C:9]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)=[N:8][N:7]([CH2:6][C:5]3[CH:30]=[CH:31][C:50]([N:49]([CH3:52])[CH3:48])=[CH:3][CH:4]=3)[C:12](=[O:13])[CH:11]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 516892Sodium BicarbonateHCID 18184436N,N-dimethylformamide acetoneHCID 183693922-(4-aminobenzyl)-5,6-bis(4-methoxyphenyl)-2H-pyridazin-3-one

Product 1

HCID 183694395,6-bis(4-methoxyphenyl)-2-[4-(dimethylamino)benzyl]-2H-pyridazin-3-oneYield 30.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(4-aminobenzyl)-5,6-bis(4-methoxyphenyl)-2H-pyridazin-3-one (245 mg, 0.6 mmol) in acetone/N,N-dimethylformamide (5/1) (6 ml), sodium hydrogencarbonate (378 mg, 4.5 mmol) and a solution of dimethyl sulfate in acetone [an acetone solution of dimethyl sulfate (631 mg) (total volume: 5 ml); 3.0 ml, 3.0 mmol)] was added, followed by stirring under heat at 60° C. for 90 minutes. After the acetone was distilled off, the residue was extracted with ethyl acetate. The organic layer was washed successively with water and a brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off. The pale orange oil (238 mg) was separated and purified by silica gel preparative chromatography [developer: chloroform/methanol (20/1)], whereby 5,6-bis(4-methoxyphenyl)-2-[4-(dimethylamino)benzyl]-2H-pyridazin-3-one (80.6 mg, 30.8%) was obtained as a reddish brown oil from fractions having large Rf values. 1H-NMR (CDCl3) δ: 2.94(6H,s), 3.79(6H,s), 5.32(2H,s), 6.71(2H,d,J=8.79 Hz), 6.78(2H,d,J=8.79 Hz), 6.79(2H,d,J=9.03 Hz), 6.85(1H,s), 7.07(2H,d,J=8.79 Hz), 7.11(2H,d,J=9.03 Hz), 7.48(2H,d,J=8.79 Hz).

Workup

  1. addition3.0 ml, 3.0 mmol)] was added
  2. distillationAfter the acetone was distilled off
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water
  5. dry with materiala brine, and was then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe pale orange oil (238 mg) was separated
  8. custompurified by silica gel preparative chromatography [developer: chloroform/methanol (20/1)]

Sources & evidence

ORD record
ord-c0ef46c51f0f41fc938030edbaead0d4
Source dataset
uspto-grants-2002_02
Patent number
US06348468B1

Reaction notes

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