Acetic Acid → 6-(2,4-Dichloro-benzenesulfonyl)-2H-pyridazin-3-one

HRID 985401Notes

Reaction equation

HRID 985401 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=1.C(OO)(=[O:19])C.C(O)(=O)C.[OH2:26]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([C:10]1[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=1)(=[O:19])=[O:26]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6585Peracetic AcidHCID 225069506-(2,4-dichloro-phenylsulfanyl)-2H-pyridazin-3-one

Product 1

HCID 98361006-(2,4-Dichloro-benzenesulfonyl)-2H-pyridazin-3-oneYield 37%

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(2,4-dichloro-phenylsulfanyl)-2H-pyridazin-3-one (418 mg), peracetic acid (3.2 mL) and acetic acid (3.2 mL) was prepared and stirred for 2.5 hours at 80° C. The reaction mixture was then cooled to room temperature and poured into water (50 mL). The resulting white solid was collected and dried to obtain the title product, 6-(2,4-dichloro-benzenesulfonyl)-2H-pyridazin-3-one, (37%, 173 mg); mp, 202-203° C.; NMR 7.15 (d, 1H), 7.81 (dd, 1H), 8.03 (m, 2H), 8.25 (d, 1H), 13.88 (s, 1H).

Workup

  1. customwas prepared
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customThe resulting white solid was collected
  4. customdried

Sources & evidence

ORD record
ord-dedd12295f414541a04c0f69d8f2f1fe
Source dataset
uspto-grants-2005_03
Patent number
US06872722B2

Reaction notes

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