Hydrochloric Acid → 6-(5-chloro-3-methyl-benzofuran-2-sulfenyl)-2H-pyridazin-3-one

HRID 1369463Notes

Reaction equation

HRID 1369463 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([S:10][C:11]3[N:16]=[N:15][CH:14]=[CH:13][CH:12]=3)=[C:7]([CH3:17])[C:6]=2[CH:18]=1.Cl.[O:20]1CCOCC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([S:10][C:11]3[CH:12]=[CH:13][C:14](=[O:20])[NH:15][N:16]=3)=[C:7]([CH3:17])[C:6]=2[CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 225915466-(5-Chloro-3-methyl-benzofuran-2-sulfenyl)-pyridazine

Product 1

HCID 98572586-(5-chloro-3-methyl-benzofuran-2-sulfenyl)-2H-pyridazin-3-oneYield 73%

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(5-chloro-3-methyl-benzofuran-2-sulfenyl)-pyridazine (1.6 mmol, 500 mg), conc. HCl (1 mL), and dioxane (5 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, and the resulting white precipitate was collected and crystallized from ethanol to obtain the desired product, 6-(5-chloro-3-methyl-benzofuran-2-sulfenyl)-2-H-pyridazin-3-one (73%, 113 mg); mp >240° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. additionWater (10 mL) was added to the residue
  4. customthe resulting white precipitate was collected
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-9b3ba939c50c4c69b8a5baf3aaa80fbf
Source dataset
uspto-grants-2003_06
Patent number
US06579879B2

Reaction notes

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