Dimethylformamide → 4-Chloro-2-(1,1-dimethylethyl)-5-[1-(4-methylphenyl)ethoxy]-3(2H)-pyridazinone

HRID 1589525Notes

Reaction equation

HRID 1589525 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[CH3:9].[C:17]([N:21]1[C:26](=[O:27])[C:25]([Cl:28])=[C:24]([OH:29])[CH:23]=[N:22]1)([CH3:20])([CH3:19])[CH3:18].CN(C)C=O>O>[C:17]([N:21]1[C:26](=[O:27])[C:25]([Cl:28])=[C:24]([O:29][CH:8]([CH3:9])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:23]=[N:22]1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5242421-(1-Chloroethyl)-4-methylbenzeneHCID 546869462-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 155901114-Chloro-2-(1,1-dimethylethyl)-5-[1-(4-methylphenyl)ethoxy]-3(2H)-pyridazinoneYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 g of anhydrous potassium carbonate and 1.3 g of 4-(α-chloroethyl)toluene were added to 1.5 g of 2-tert.-butyl-4-chloro-5-hydroxy-3(2H)-pyridazinone dissolved into 10 ml of N,N-dimethylformamide, and the resulting mixture was heated under stirring in an oil bath of 80° to 110° C. for 4 hours. After being allowed to cool to room temperature, 100 ml of water was added to the reaction mixture, followed by stirring. Oily matter separated from the reaction mixture was extracted with 50 ml of chloroform. The aqueous layer was extracted with 30 ml of chloroform again, the chloroform layers were combined, washed with water, and dried over anhydrous sodium sulfate. Chloroform was distilled off under reduced pressure, and the residue was recrystallized from isopropyl ether-petroleum ether mixer to obtain 1.1 g of the intended compound (Compound No. 1.78) having m.p. 104°-105.5° C. (yield: 48.1%)

Workup

  1. temperaturethe resulting mixture was heated
  2. stirringby stirring
  3. customOily matter separated from the reaction mixture
  4. extractionwas extracted with 50 ml of chloroform
  5. extractionThe aqueous layer was extracted with 30 ml of chloroform again
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationChloroform was distilled off under reduced pressure
  9. customthe residue was recrystallized from isopropyl ether-petroleum ether mixer

Sources & evidence

ORD record
ord-d316ebea6fcf407aaaaae4c8110d334c
Source dataset
uspto-grants-1986_02
Patent number
US04571397

Reaction notes

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