Water → 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethylphenoxy) ethylthio]-3-(2H)-pyridazinone

HRID 1164789Notes

Reaction equation

HRID 1164789 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][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:16]=1[O:17][CH2:18][CH2:19]Br.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][CH2:19][CH2:18][O:17][C:16]2[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:15]=2[CH3:14])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24522082-(2-Bromoethoxy)-1,3-dimethylbenzeneHCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinone

Product 1

HCID 146229592-t-butyl-4-chloro-5-(2'-[2",6"-dimethylphenoxy) ethylthio]-3-(2H)-pyridazinoneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.3 g of 2-(2',6'-dimethylphenoxy)ethyl bromide, and thereto were added 1.1 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give crystals. The crystals thus obtained were washed with n-hexane to give 3.5 g of the intended compound. m.p. 104.3°~105.2° C.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customto give crystals
  4. customThe crystals thus obtained
  5. washwere washed with n-hexane

Sources & evidence

ORD record
ord-22fd11b800904dad95de3e2b6e1d2aba
Source dataset
uspto-grants-1990_03
Patent number
US04906627

Reaction notes

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