Water → 2-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-3(2H)-pyridazinone

HRID 2352019Notes

Reaction equation

HRID 2352019 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][SH:14])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]([N:21]1[C:26](=[O:27])[C:25]([CH3:28])=[C:24](Cl)[CH:23]=[N:22]1)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[C:17]([N:21]1[C:26](=[O:27])[C:25]([CH3:28])=[C:24]([S:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:16][CH:15]=2)[CH:23]=[N:22]1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-oneHCID 15147117(1,1'-Biphenyl)-4-methanethiol

Product 1

HCID 138250992-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-3(2H)-pyridazinoneYield 44.7%

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 added dropwise with a solution of 3.2 g of p-phenylbenzyl mercaptan dissolved in 15 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 3.2 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone 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 sodium sulfate, and freed of solvent by distillation under reduced pressure to give 4.8 g of crude product. The crude product was recrystallized from 5 ml of hexane to obtain 2.6 g of 2-t-butyl-4-methyl-5-(p-phenyl-benzylthio)-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 sodium sulfate
  7. distillationfreed of solvent by distillation under reduced pressure
  8. customto give 4.8 g of crude product
  9. customThe crude product was recrystallized from 5 ml of hexane

Sources & evidence

ORD record
ord-d012267afa3a4c9bba7012298758936d
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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