2-Chloroethanol → HCID 12688574, compound

HRID 1732648Notes

Reaction equation

HRID 1732648 reaction equation
[C:1]1([C:7]2[C:8](=[O:25])[NH:9][N:10]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[OH-].[Na+].Cl[CH2:34][CH2:35][OH:36]>O>[OH:36][CH2:35][CH2:34][N:9]1[C:8](=[O:25])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:10]1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 3599665HCID 3599665, compound

Product 1

HCID 12688574HCID 12688574, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4,5,6-triphenyl-2H-pyridazin-3-one (6.0 g) were added 50 ml of dimethylformamide and a solution of sodium hydroxide pellets (0.7 g) dissolved in 5 ml of water. The resultant slurry was stirred at room temperature, while adding dropwise, 1.5 g of 2-chloroethanol. The mixture was heated to 110° C. for 1 hour and then allowed to heat for 16 hours at 90° C., after which time, the dimethylformamide was removed by evacuation. The residue was redissolved in methanol from which the compound was triturated, filtered and washed with petroleum ether to obtain the title compound (25 percent yield), m.p. 189° C. (dec).

Workup

  1. additionwhile adding dropwise
  2. temperatureThe mixture was heated to 110° C. for 1 hour
  3. temperatureto heat for 16 hours at 90° C.
  4. customafter which time, the dimethylformamide was removed by evacuation
  5. dissolutionThe residue was redissolved in methanol from which the compound
  6. customwas triturated
  7. filtrationfiltered
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-6cd112bbb4c24225bfd38133c2bb0262
Source dataset
uspto-grants-1980_12
Patent number
US04238490

Reaction notes

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