3-Pyridinemethanamine → 4-chloro-6-[3-(phenylthio)propyloxy]-5-(3-picolylamino)-3(2H)-pyridazinone

HRID 1451230Notes

Reaction equation

HRID 1451230 reaction equation
[Cl:1][C:2]1[C:3](=[O:20])[NH:4][N:5]=[C:6]([O:9][CH2:10][CH2:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]=1Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH2:28])[CH:22]=1>O.O1CCOCC1>[Cl:1][C:2]1[C:3](=[O:20])[NH:4][N:5]=[C:6]([O:9][CH2:10][CH2:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]=1[NH:28][CH2:27][C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 199743804,5-dichloro-6-[3-(phenylthio)propyloxy]-3(2H)-pyridazinone

Product 1

HCID 199743864-chloro-6-[3-(phenylthio)propyloxy]-5-(3-picolylamino)-3(2H)-pyridazinoneYield 74.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

After 0.3 g of 4,5-dichloro-6-[3-(phenylthio)propyloxy]-3(2H)-pyridazinone and 0.243 g of 3-picolylamine were dissolved in a solvent mixture of water-dioxane (1:1), the mixture was heated to reflux for 8 hours. After completion of the reaction, the reaction mixture was poured onto water and extracted with ethyl acetate. After washing with water and drying, the solvent was distilled off. The resulting crystals were recrystallized from isopropanol to give 0.273 g of the objective compound. Yield, 73%, Melting point, 152°-155° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 hours
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was poured onto water
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. customdrying
  8. distillationthe solvent was distilled off
  9. customThe resulting crystals were recrystallized from isopropanol

Sources & evidence

ORD record
ord-ab40284cf5614140a0b8411018b35e34
Source dataset
uspto-grants-1997_02
Patent number
US05604226

Reaction notes

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