Dimethyl Sulfoxide → 2-(propylsulfonylaminomethyl)-5-[pyridazin-3(2H)-on-6-yl]indane

HRID 2293100Notes

Reaction equation

HRID 2293100 reaction equation
Br.C(O)(=O)C.CS(C)=O.[CH2:10]([S:13]([NH:16][CH2:17][CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:27]3[CH2:28][CH2:29][C:30](=[O:33])[NH:31][N:32]=3)[CH:24]=2)[CH2:19]1)(=[O:15])=[O:14])[CH2:11][CH3:12].C(OC(C)C)(C)C>C(O)(=O)C>[CH2:10]([S:13]([NH:16][CH2:17][CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:27]3[CH:28]=[CH:29][C:30](=[O:33])[NH:31][N:32]=3)[CH:24]=2)[CH2:19]1)(=[O:15])=[O:14])[CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7914Diisopropyl EtherHCID 21476308HCID 21476308, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 214763052-(propylsulfonylaminomethyl)-5-[pyridazin-3(2H)-on-6-yl]indaneYield 92.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

25 ml of 30% hydrogen bromide-acetic acid and 1.3 ml of dimethyl sulfoxide were added to 5.24 g of 2-(propylsulfonylaminomethyl)-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane suspended in 60 ml of acetic acid. The mixture was stirred at room temperature for 2 hours. 150 ml of isopropyl ether was added to the mixture, and crystals precipitated were collected by filtration, washed with water, dried and then recrystallized from methanol to obtain 4.82 g of 2-(propylsulfonylaminomethyl)-5-[pyridazin-3(2H)-on-6-yl]indane. This compound had the same physical properties as those of the compound obtained in Example 2.

Workup

  1. customprecipitated
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-027cb871a4a2459f964b157995424a9c
Source dataset
uspto-grants-1997_11
Patent number
US05686452

Reaction notes

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