Dimethylformamide → HCID 13822279, compound

HRID 1904252Notes

Reaction equation

HRID 1904252 reaction equation
CN(C)C=O.[Cl:6][C:7]1[C:8](=[O:16])[N:9]([CH2:14][CH3:15])[N:10]=[CH:11][C:12]=1[OH:13].Br[CH2:18][C:19]1[S:20][C:21]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[C:8](=[O:16])[N:9]([CH2:14][CH3:15])[N:10]=[CH:11][C:12]=1[O:13][CH2:18][C:19]1[S:20][C:21]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14671827HCID 14671827, compoundHCID 546807714-Chloro-2-ethyl-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 13822279HCID 13822279, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of N,N-dimethylformamide were added 1.9 g of 4-chloro-2-ethyl-5-hydroxy-3(2H)-pyridazinone, 3.2 g of 2-bromomethyl-5-(4-chlorobenzoyl)-thiophene and 1.5 g of potassium carbonate, and the mixture was stirred at 50° to 60° C. for 2 hours. After cooling, the reaction mixture was poured into 50 ml of water and extracted twice with 50 ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to obtain 4.0 g of a crude product. The crude product was recrystallized from 2-propanol to obtain 3.1 g of 4-chloro-5-[{5-(4-chlorobenzoyl)-2-thienyl}-methyloxy]-2-ethyl-3(2H)-pyridazinone, m.p. 168.0°~168.5° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 50 ml of benzene
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationfreed of solvent by distillation under reduced pressure
  6. customto obtain 4.0 g of a crude product
  7. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-c9372d9746664f00ad9f4a38f50dbec0
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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