Hydrochloric Acid → 6-(5-Chloro-3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin 2H-pyridazin-3-one

HRID 1369465Notes

Reaction equation

C[O:2][C:3]1[N:4]=[N:5][C:6]([S:9]([C:12]2[O:13][C:14]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:15]=3[C:16]=2[CH3:17])(=[O:11])=[O:10])=[CH:7][CH:8]=1.Cl>O1CCOCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:14]2[O:13][C:12]([S:9]([C:6]3[NH:5][NH:4][CH:3]=[CH:8][CH:7]=3)(=[O:10])=[O:11])=[C:16]([CH3:17])[C:15]=2[CH:18]=1.[N:5]1[NH:4][C:3](=[O:2])[CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-methoxy-6-(5-chloro-3-methyl-benzofuran-2-sulfonyl)-pyridazine (22.2 mmol, 7.5 g), conc. HCl (5 mL), and dioxane (50 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled and evaporated to dryness. Water (20 mL) was added to the residue. The resulting precipitate was collected and crystallized from ethanol to obtain the desired product: 6-(5-chloro-3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-2H-pyridazin-3-one (89%, 6.42 g).

Workup

temperatureThe reaction mixture was cooled
customevaporated to dryness
additionWater (20 mL) was added to the residue
customThe resulting precipitate was collected
customcrystallized from ethanol

Sources & evidence

ORD record: ord-29d7953f25b44b04be44efe3378627bf
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579879B2

Reaction notes

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