Sodium Hydroxide → 6-(4-Amino-2,6-dichloro-phenylsulfanyl)-4-isopropyl-2H-pyridazin-3-one

HRID 2199160Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:20]C(=O)C)[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:18])[NH:11][N:10]=1.[OH-].[Na+]>CO.O>[NH2:20][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([S:8][C:9]2[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[C:12](=[O:18])[NH:11][N:10]=2)=[C:6]([Cl:19])[CH:5]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamide (84) (4.0 g, 10.7 mmol) in methanol (15 mL) and water (15 mL) was treated with powdered sodium hydroxide (2.14 g, 53.5 mmol). The reaction was then heated to reflux for 18 h. At this time, the reaction was cooled to 25° C., diluted with water (500 mL) and extracted with ethyl acetate (3×300 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×200 mL), dried with magnesium sulfate, filtered and concentrated under vacuum to afford 6-(4-amino-2,6-dichloro-phenyl sulfanyl)-4-isopropyl-2H-pyridazin-3-one (85) (3.5 g, 99%) as a light tan solid. The material was used without further purification; ES(+)-HRMS m/e calcd for C13H13Cl2N3OS (M+H)+ 330.0229, found 330.0229. Exact Mass=329.0156; Molecular weight=330.24

Workup

temperatureThe reaction was then heated
temperatureto reflux for 18 h
extractionextracted with ethyl acetate (3×300 mL)
washThe organics were washed with a saturated aqueous sodium chloride solution (1×200 mL)
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-d05f6bbf305646a4a377980b968e4b22
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE046024E1

Reaction notes

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