Carbon Dioxide → 4-Acetyl-2-(2'-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one

HRID 1732645Notes

Reaction equation

HRID 1732645 reaction equation
[C:1]([C:4]1[C:5](=[O:24])[NH:6][N:7]=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].C1(=O)O[CH2:28][CH2:27][O:26]1.[OH-].[K+].C(=O)=O>CN(C)C=O.O>[OH:26][CH2:27][CH2:28][N:6]1[C:5](=[O:24])[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:7]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7303Ethylene carbonateHCID 14797Potassium HydroxideHCID 43908775643-31-1

Product 1

HCID 1007114-Acetyl-2-(2'-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-oneYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

The compound of Example 1 (3.1 g), ethylene carbonate (2.0 g), and potassium hydroxide (powdered) were dissolved in dimethylformamide (50 ml) and the flask placed in an oil bath (110°-120° C.) until CO2 evolution ceased (ca. 3.5 hours). The reaction mixture was poured into water (400 ml) and chilled at 5° C. for 1 hour. The resulting precipitate was separated by filtration and recrystallized from methanol (85 ml) to obtain the title compound (68 percent yield) as pale yellow crystals, m.p. 191°-193° C.

Workup

  1. customthe flask placed in an oil bath
  2. custom(110°-120° C.)
  3. custom(ca. 3.5 hours)
  4. customThe resulting precipitate was separated by filtration
  5. customrecrystallized from methanol (85 ml)

Sources & evidence

ORD record
ord-6de8f16d4dc24b03a17d72599c27a62b
Source dataset
uspto-grants-1980_12
Patent number
US04238490

Reaction notes

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