Water → 2-t-butyl-5-(alpha-ethyl-p-t-butylbenzylthio)-4-methyl-3(2H)-pyridazinone

HRID 2352022Notes

Reaction equation

HRID 2352022 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([SH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([CH:16](Cl)[C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=1)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C(OCC)(=O)C.C1C=CC=CC=1>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([S:13][CH:16]([CH2:14][CH3:15])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 138222652-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinoneHCID 146742671-(tert-Butyl)-4-(1-chloropropyl)benzene

Product 1

HCID 138251252-t-butyl-5-(alpha-ethyl-p-t-butylbenzylthio)-4-methyl-3(2H)-pyridazinoneYield 53.7%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.8 g (0.004 mol) of 2-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone and 0.84 g (0.004 mol) of α-ethyl-p-t-butylbenzyl chloride dissolved in 20 ml of N,N-dimethylformamide was added 1.0 g (0.01 mol) of sodium carbonate at room temperature under stirring. After addition, the resulting mixture was stirred at 70°~80° C. for four hours. After allowed to cool, the reaction mixture was poured into 200 ml of water and then extracted with 100 ml of benzene. The resulting benzene layer was washed with 100 ml of water, dried over anhydrous sodium sulfate, and freed of solvent by distillation to give 1.5 g of crude product. The crude product was fractionated on silica gel column chromatography [developer: a mixed solvent of benzene and ethyl acetate (10:1 mixture)] to obtain 0.8 g of 2-t-butyl-5-(α-ethyl-p-t-butylbenzylthio)-4-methyl-3(2H)-pyridazinone.

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was stirred at 70°~80° C. for four hours
  3. temperatureto cool
  4. extractionextracted with 100 ml of benzene
  5. washThe resulting benzene layer was washed with 100 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationfreed of solvent by distillation
  8. customto give 1.5 g of crude product

Sources & evidence

ORD record
ord-9e97fee86de24cd3bfa400bc7b22559a
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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