Hydrochloric Acid → 6-(3-Methylbenzofuran-2-sulfonyl)-2h-pyridazin-3-one

HRID 22731Notes

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-methoxy-6-(5-chloro-3-methyl-benzofuran-2-sulfonyl)-pyridazine (0.5 mmol, 162 mg), conc. HCl (1 mL), and dioxane (3 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled and evaporated to dryness. Water (10 mL) was added to the residue. The resulting yellow precipitate was collected and crystallized from ethanol to obtain the desired product: 6-(3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one (73%, 113 mg); mp 247° C.-248° C.

Workup

temperatureThe reaction mixture was cooled
customevaporated to dryness
additionWater (10 mL) was added to the residue
customThe resulting yellow precipitate was collected
customcrystallized from ethanol

Sources & evidence

ORD record: ord-70e8f8934bc547028c7497a30ce47799
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849629B2

Reaction notes

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