Triethylamine → 4,5-dichloro-6-[3-(phenylthio)propyloxy]-3(2H)-pyridazinone

HRID 1451229Notes

Reaction equation

HRID 1451229 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:12][C:13]1[C:14](=[O:21])[NH:15][N:16]=[C:17]([OH:20])[C:18]=1[Cl:19].C(N(CC)CC)C>CN(C)C=O>[Cl:12][C:13]1[C:14](=[O:21])[NH:15][N:16]=[C:17]([O:20][CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:18]=1[Cl:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70618473-Bromopropyl phenyl sulfideHCID 178518839HCID 178518839, compound

Product 1

HCID 199743804,5-dichloro-6-[3-(phenylthio)propyloxy]-3(2H)-pyridazinoneYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 1.57 g of 1-bromo-3-phenylthiopropane, 2 g of 4,5-dichloro-6-hydroxy-3(2H)-pyridazinone and 1.3 g of triethylamine were dissolved in dimethylformamide, the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured onto water. The formed crystals were taken by filtration and thoroughly washed with water. The crystals were recrystallized from ethanol to give 1.5 g of the objective compound. Yield, 52%, Melting point, 187°-188° C.

Workup

  1. additionThe reaction mixture was poured onto water
  2. filtrationThe formed crystals were taken by filtration
  3. washthoroughly washed with water
  4. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-ce26d6e61583406e996a61aab7cd2a1a
Source dataset
uspto-grants-1997_02
Patent number
US05604226

Reaction notes

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