Water → 2-t-butyl-5-(p-chlorobenzyloxy)-4-ethyl-3(2H)-pyridazinone

HRID 2352025Notes

Reaction equation

HRID 2352025 reaction equation
[H-].[Na+].[C:3]([N:7]1[C:12](=[O:13])[C:11]([CH2:14][CH3:15])=[C:10](Cl)[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=1.O>CN(C)C=O>[C:3]([N:7]1[C:12](=[O:13])[C:11]([CH2:14][CH3:15])=[C:10]([O:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 138250102-t-butyl-5-chloro-4-ethyl-3(2H)-pyridazinone

Product 1

HCID 138250042-t-butyl-5-(p-chlorobenzyloxy)-4-ethyl-3(2H)-pyridazinoneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 10 ml of dry N,N-dimethylformamide was added 0.75 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 2.2 g of 2-t-butyl-5-chloro-4-ethyl-3(2H)-pyridazinone dissolved in 15 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 1.4 g of p-chlorobenzyl alcohol dissolved in 15 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was reacted at 80° C. for one hour. The resulting solution was poured into 50 ml of water and extracted twice with 50 ml of diethyl ether. The resulting organic layer was dried over anhydrous sulfate and freed of solvent by distillation under reduced pressure to give a crude product. The crude product was recrystallized from hexane to obtain 2.4 g of 2-t-butyl-5-(p-chlorobenzyloxy)-4-ethyl-3(2H)-pyridazinone.

Workup

  1. customwas kept at 0° C.
  2. waitAfter ten minutes passed
  3. additionAfter completion of dropwise addition
  4. customthe resulting mixture was reacted at 80° C. for one hour
  5. extractionextracted twice with 50 ml of diethyl ether
  6. dry with materialThe resulting organic layer was dried over anhydrous sulfate
  7. distillationfreed of solvent by distillation under reduced pressure
  8. customto give a crude product
  9. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-b8d1771d00684f7ba5917574cd321145
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

Loading…