Phenol → HCID 66695552, compound

HRID 579264Notes

Reaction equation

HRID 579264 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[H-].[Na+].[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[C:28]1[C:29](=[O:40])[N:30]([CH3:39])[N:31]=[C:32]([CH3:38])[C:33]=1S(C)(=O)=O)[CH3:18]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.CS(C)=O>[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[C:28]1[C:29](=[O:40])[N:30]([CH3:39])[N:31]=[C:32]([CH3:38])[C:33]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:18]

Participants

8

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 24758Sodium hydrideHCID 569427174-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

Product 1

HCID 66695552HCID 66695552, compoundYield 29.3%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a test tube (outside diameter: 21 mm Φ×overall length: 160 mm), phenol (108 mg), toluene (930 mg), and 60% of oily sodium hydride (44 mg) were added, and stirred at room temperature for 5 minutes. To the mixture, (4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydropyridazin-3-one ((2-34)-(1)-39) (299 mg) was added, and stirred at room temperature for 1.5 hours and at 100° C. for 1.5 hours. To the mixture, benzyltriethylammonium chloride was added and stirred for 1.5 hours, and then DMSO (1.1 ml) was added and stirred for 2 hours. After the mixture was cooled to room temperature, water was added and extracted with toluene 3 times. The organic layers were combined, washed with 2N aqueous sodium hydroxide solution 3 times, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=3:1) to give 91 mg of 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-phenoxy-2,3-dihydro-3-pyridazinone ((1-31)-(1)-39).

Workup

  1. stirringstirred at room temperature for 1.5 hours and at 100° C. for 1.5 hours
  2. stirringstirred for 1.5 hours
  3. stirringstirred for 2 hours
  4. temperatureAfter the mixture was cooled to room temperature
  5. extractionextracted with toluene 3 times
  6. washwashed with 2N aqueous sodium hydroxide solution 3 times
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ce053ce01f44055bb13f426bcb44f4e
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

Loading…