Sodium hydride → HCID 13825121, compound

HRID 2352021Notes

Reaction equation

HRID 2352021 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][SH:12])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[C:15]([N:19]1[C:24](=[O:25])[C:23]([CH3:26])=[C:22](Cl)[CH:21]=[N:20]1)([CH3:18])([CH3:17])[CH3:16]>O1CCCC1>[C:15]([N:19]1[C:24](=[O:25])[C:23]([CH3:26])=[C:22]([S:12][CH2:11][C:10]2[CH:9]=[CH:8][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[CH:14][CH:13]=2)[CH:21]=[N:20]1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27572524-tert-Butylbenzyl mercaptanHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

Product 1

HCID 13825121HCID 13825121, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 30 ml of dry tetrahydrofuran was added 0.5 g of 55% sodium hydride. The resulting mixture was kept at room temperature and added dropwise with a solution of 1.8 g of p-t-butylbenzyl mercaptan dissolved in 10 ml of tetrahydrofuran. After ten minutes passed, the resulting mixture was added dropwise with a solution of 2.0 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone dissolved in 10 ml of tetrahydrofuran. After completion of dropwise addition, the resulting mixture was reacted for 2 hours under heat-reflux. After the reaction mixture was concentrated under reduced pressure, it 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 3.5 g of crude product. The crude product was recrystallized from 5 ml of hexane to obtain 1.6 g of 2-t-butyl-5-(p-t-butylbenzylthio)-4-methyl-3(2H)-pyridazinone.

Workup

  1. customwas kept at room temperature
  2. waitAfter ten minutes passed
  3. additionAfter completion of dropwise addition
  4. customthe resulting mixture was reacted for 2 hours
  5. temperatureunder heat-reflux
  6. concentrationAfter the reaction mixture was concentrated under reduced pressure, it
  7. additionwas poured into 50 ml of water
  8. extractionextracted twice with 50 ml of diethyl ether
  9. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  10. distillationfreed of solvent by distillation under reduced pressure
  11. customto give 3.5 g of crude product
  12. customThe crude product was recrystallized from 5 ml of hexane

Sources & evidence

ORD record
ord-a12fe625ec4640eabcbe5995763df3cf
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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