Sodium Hydroxide → N-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamide

HRID 2199159Notes

Reaction equation

HRID 2199159 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[N:10]=[N:11][C:12](Cl)=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1.[C:21]([O-])(=[O:23])[CH3:22].[Na+].[OH-:26].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][C:21](=[O:23])[CH3:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:26])[NH:11][N:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 59834470HCID 59834470, compound

Product 1

HCID 59834497N-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenylamine (83) (1.23 g, 3.50 mmol) in glacial acetic acid (35 mL) was treated with sodium acetate (1.0 g, 12.25 mmol). This mixture was heated to 95° C. for 18 h. At this time, the reaction mixture was cooled to 25° C., poured onto water (200 mL) and neutralized with a 3N aqueous sodium hydroxide solution. This solution was then extracted with ethyl acetate (2×200 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate, filtered and concentrated under vacuum to afford N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yl-sulfanyl)-phenyl]-acetamide (84) (1.3 g, 99%) as an off-white solid. This material was used without further purification; ES(+)-HRMS m/e calcd for C15H15Cl2N3O2S (M+H)+ 372.0335, found 372.0335. Exact Mass=371.0262; Molecular weight=372.28

Workup

  1. temperatureAt this time, the reaction mixture was cooled to 25° C.
  2. additionpoured onto water (200 mL)
  3. extractionThis solution was then extracted with ethyl acetate (2×200 mL)
  4. washThe combined organics were washed with a saturated aqueous sodium chloride solution (1×100 mL)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2ccfc1231bc0422e921b6c8ee98529f1
Source dataset
uspto-grants-2016_06
Patent number
USRE046024E1

Reaction notes

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