Water → 2-t-butyl-4-chloro-5-[4-(2-methoxyethoxy)-benzylthio]-3(2H)-pyridazinone

HRID 1904235Notes

Reaction equation

HRID 1904235 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([SH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][O:15][CH3:14])=[CH:26][CH:25]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinoneHCID 146717951-Bromomethyl-4-(2-methoxy-ethoxy)-benzene

Product 1

HCID 146717962-t-butyl-4-chloro-5-[4-(2-methoxyethoxy)-benzylthio]-3(2H)-pyridazinoneYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of 95% ethanol were dissolved 1.5 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 1.85 g of 4-(2-methoxyethoxy)benzyl bromide, and then 0.48 g of anhydrous sodium carbonate was added thereto. The resulting mixture was stirred overnight at room temperature, poured into water, extracted with benzene, washed with water and dried over anhydrous sodium sulfate. Benzene was distilled off under reduced pressure and the resulting solid was recrystallized from n-hexane-benzene to obtain 1.64 g of the aimed compound, m.p. 105.6°~107.3° C.

Workup

  1. extractionextracted with benzene
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationBenzene was distilled off under reduced pressure
  5. customthe resulting solid was recrystallized from n-hexane-benzene

Sources & evidence

ORD record
ord-5b45406a25aa4681b7349623965f07c7
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

Loading…