Triethylamine → HCID 13193374, compound

HRID 463651Notes

Reaction equation

HRID 463651 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][O:17][CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20].C(N(CC)CC)C>CC(C)=O>[CH3:16][O:17][CH:18]([CH2:22][CH3:23])[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 161928Ici 109,081HCID 138193982-Methoxybutanoyl chloride

Product 1

HCID 13193374HCID 13193374, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.3 g (0.1 mole) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone were stirred with 18.1 g (0.12 mole) of 2-methoxybutyryl chloride and 10.1 g (0.1 mole) of triethylamine in 200 ml of absolute acetone for 3 hours at room temperature. 100 g of ice were added, the crystals were filtered off under suction and recrystallized from dimethylformamide/water, and the resulting product was dried at 50° C. under greatly reduced pressure. 18.9 g (63%) of 6-[p-(2-methoxybutyrylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained. Mp.: 151°-152° C.

Workup

  1. filtrationthe crystals were filtered off under suction
  2. customrecrystallized from dimethylformamide/water
  3. customthe resulting product was dried at 50° C. under greatly reduced pressure

Sources & evidence

ORD record
ord-4cc8df5ab5054ceaa7efc5a7f17bb802
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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