Triethylamine → HCID 13193384, compound

HRID 463656Notes

Reaction equation

HRID 463656 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.[C:16]([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])#[N:17].C(N(CC)CC)C>CC(C)=O>[C:16]([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])#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 161928Ici 109,081HCID 12224884Butanoyl chloride, 2-cyano-

Product 1

HCID 13193384HCID 13193384, compoundYield 50%

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 15.8 g (0.12 mole) of 2-cyanobutyryl 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, after which the crystals were filtered off under suction, and the product was recrystallized from dimethylformamide/water and dried at 50° C. under greatly reduced pressure. 14.9 g (50%) of 6-[p-(2-cyanobutyrylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained. Mp.: 225°-227° C.

Workup

  1. filtrationafter which the crystals were filtered off under suction
  2. customthe product was recrystallized from dimethylformamide/water
  3. customdried at 50° C. under greatly reduced pressure

Sources & evidence

ORD record
ord-4ace6d9153d04632a2d27c259d06afa8
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

Loading…