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

HRID 22732Notes

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-42e5f900598f452da816d1574fcbd6b2
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849629B2

Reaction notes

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