Water → HCID 13488670, compound

HRID 1494522Notes

Reaction equation

HRID 1494522 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].[F:14][C:15]([F:32])([F:31])[C:16]1[CH:30]=[CH:29][C:19]([O:20][C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]3[CH:29]=[CH:30][C:16]([C:15]([F:14])([F:31])[F:32])=[CH:17][CH:18]=3)=[CH:28][CH:27]=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 14720261HCID 14720261, compound

Product 1

HCID 13488670HCID 13488670, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide were dissolved 2.2 g (0.01 mol) of 2-tert.-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 3.5 g (0.0105 mol) of 4-(4'-trifluoromethylphenoxy) benzyl bromide, and thereto was added 2.1 g (0.02 mol) of anhydrous sodium carbonate to effect reaction at 85° to 90° C. for 4 hours. After the reaction, the reaction liquid was allowed to cool, poured into water and then extracted with benzene. The benzene layer was washed with 5% aqueous solution of sodium hydroxide and then with water, dried over anhydrous sodium sulfate and then freed of benzene by distillation under reduced pressure. The oily residue was incorporated with n-hexane and the precipitated crystals were filtered off to obtain white crystals (yield: 85.5%).

Workup

  1. customreaction at 85° to 90° C. for 4 hours
  2. customAfter the reaction
  3. customthe reaction liquid
  4. temperatureto cool
  5. extractionextracted with benzene
  6. washThe benzene layer was washed with 5% aqueous solution of sodium hydroxide
  7. dry with materialwith water, dried over anhydrous sodium sulfate
  8. distillationfreed of benzene by distillation under reduced pressure
  9. filtrationthe precipitated crystals were filtered off

Sources & evidence

ORD record
ord-fa37acf0f55847e0bb1acf38cb41b4b6
Source dataset
uspto-grants-1991_06
Patent number
US05026850

Reaction notes

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