N-methyl-2-pyrrolidone → HCID 89654001, compound

HRID 335434Notes

Reaction equation

HRID 335434 reaction equation
[CH2:1]([C:3]1([C:13]2[C:14](=[O:25])[N:15]([CH3:24])[N:16]=[C:17]([CH3:23])[C:18]=2S(C)(=O)=O)[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[CH2:4]1)[CH3:2].CN1CCCC1=[O:32].[OH-].[Na+]>O>[CH2:1]([C:3]1([C:13]2[C:14](=[O:25])[N:15]([CH3:24])[N:16]=[C:17]([CH3:23])[C:18]=2[OH:32])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 89653993HCID 89653993, compound

Product 1

HCID 89654001HCID 89654001, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a 1 L volume four-necked flask, 4-(1,3,5-triethylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-40) (98.5 g) and N-methyl-2-pyrrolidone (383 ml) were added at room temperature. Sodium hydroxide (43.5 g) dissolved in water (118 ml) and a container washing solution (39 ml of water×2) were added at room temperature. The mixture was heated to 70±2° C., and stirred for 6 hours. To the mixture, toluene (300 ml) and water (500 ml) were added. After the mixture was stirred vigorously, additional toluene (300 ml) was added. The organic layer was removed and ice-water (500 ml) was added to the aqueous layer. pH was adjusted to 1-2 with 20 w/w % of sulfuric acid below 20° C. The precipitated solids were collected by filtration and washed with water. After air-drying, the solids were dissolved in ethyl acetate, and dried over anhydrous sodium sulfate. The insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The resulting crude product was purified by recrystallization (ethyl acetate-hexane) to give 78.0 g of 4-(1,3,5-triethylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-40).

Workup

  1. washa container washing solution (39 ml of water×2)
  2. additionwere added at room temperature
  3. additionTo the mixture, toluene (300 ml) and water (500 ml) were added
  4. stirringAfter the mixture was stirred vigorously
  5. additionadditional toluene (300 ml) was added
  6. customThe organic layer was removed
  7. additionice-water (500 ml) was added to the aqueous layer
  8. customof sulfuric acid below 20° C
  9. filtrationThe precipitated solids were collected by filtration
  10. washwashed with water
  11. customAfter air-drying
  12. dissolutionthe solids were dissolved in ethyl acetate
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe insolubles were removed by filtration
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customThe resulting crude product was purified by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-298ec7c7654d42c695924b94b2ea3e32
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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