1-(Methylsulphonyl)acetone → 4-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

HRID 335461Notes

Reaction equation

HRID 335461 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=O)[C:13]([N:15]([CH3:17])[NH2:16])=[O:14])[CH3:2].[CH3:19][S:20]([CH2:23][C:24](=O)[CH3:25])(=[O:22])=[O:21]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:14])[N:15]([CH3:17])[N:16]=[C:24]([CH3:25])[C:23]=1[S:20]([CH3:19])(=[O:22])=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 786951-(Methylsulphonyl)acetoneHCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

Product 1

HCID 569427174-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinoneYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

To a 25 mL volume three-necked flask with Dean-Stark, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39) (1.01 g), 1-methylsulfonyl-2-propanone (7-2-1) (613 mg), and toluene (2.9 ml) were added under a nitrogen atmosphere. Water was removed by azeotropic distillation at 60° C. under 100 mmHg for 4 hours. The mixture was concentrated under reduced pressure. To the residue, toluene (1.73 g) and methanol (1.90 ml) were added, then lithium hydroxide monohydrate (80 mg) was added at 0° C. After the mixture was stirred at 0° C. for 4 hours and at 5° C. for 20 hours, 20 w/w % of sulfuric acid was added to adjust pH to less than 1. To the mixture was added toluene and water, and then the organic layer was removed. The aqueous layer was extracted with toluene 2 times. The organic layers were combined, and concentrated under reduced pressure to give 1.28 g of 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-39).

Workup

  1. customWater was removed by azeotropic distillation at 60° C. under 100 mmHg for 4 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionTo the residue, toluene (1.73 g) and methanol (1.90 ml) were added
  4. additionlithium hydroxide monohydrate (80 mg) was added at 0° C
  5. addition20 w/w % of sulfuric acid was added
  6. additionTo the mixture was added toluene and water
  7. customthe organic layer was removed
  8. extractionThe aqueous layer was extracted with toluene 2 times
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2c61fa38d5a4d82862ef8aa79c665ef
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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