Water → HCID 13825156, compound

HRID 2352026Notes

Reaction equation

HRID 2352026 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].Cl[C:16]1[CH:21]=[N:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]=1[CH3:25].O>CN(C)C=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][S:12][C:16]2[CH:21]=[N:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]=2[CH3:25])=[CH:13][CH:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27572524-tert-Butylbenzyl mercaptanHCID 13825165HCID 13825165, compound

Product 1

HCID 13825156HCID 13825156, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 3 ml of dry N,N-dimethylformamide was added 0.024 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 1 g of p-t-butylbenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 0.67 g of 5-chloro-2-ethyl-4-methyl-3(2H)-pyridazinone dissolved in 5 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was allowed to stand over night. The resulting solution was poured into 30 ml of water and extracted twice with 30 ml of diethyl ether. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product. The crude product was separated and purified by thin layer chromatography (silica gel, benzene) to obtain 0.69 g of 5-(p-t-butylbenzylthio)-2-ethyl-4-methyl-3(2H)-pyridazinone.

Workup

  1. customwas kept at 0° C.
  2. waitAfter ten minutes passed
  3. additionAfter completion of dropwise addition
  4. waitto stand over night
  5. extractionextracted twice with 30 ml of diethyl ether
  6. washThe resulting organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationfreed of solvent by distillation under reduced pressure
  9. customto give 1.42 g of a crude product
  10. customThe crude product was separated
  11. custompurified by thin layer chromatography (silica gel, benzene)

Sources & evidence

ORD record
ord-d1bc0cd0a7c84ac0a3064f9f9fc721cd
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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