Water → HCID 13825114, compound

HRID 2352020Notes

Reaction equation

HRID 2352020 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][SH:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5].[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].O>CN(C)C=O>[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]([O:6][CH2:3][CH2:4][CH3:5])=[CH:14][CH:13]=2)[CH:21]=[N:20]1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12347047HCID 12347047, compoundHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

Product 1

HCID 13825114HCID 13825114, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 5 ml of dry N,N-dimethylformamide was added 0.24 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and added dropwise with a solution of 0.91 g of p-propoxybenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 1.0 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone dissolved in 5 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was reacted at room temperature for four hours. 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 1.7 g of crude product. The crude product was fractionated on thin layer chromatography to obtain 0.8 g of 2-t-butyl-4-methyl-5-(p-propoxybenzylthio)-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 room temperature for four hours
  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 1.7 g of crude product

Sources & evidence

ORD record
ord-e0de9ee4f34d487f8f8d5660ffd879ae
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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