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

HRID 1369464Notes

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-0bbf227bfae04ebab8d4f53440a3d024
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579879B2

Reaction notes

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