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

HRID 1077426Notes

Reaction equation

HRID 1077426 reaction equation
Br.C(O)(=O)C.[C:6]([NH:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21]3[CH2:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=3)[CH:18]=2)[CH2:13]1)(=[O:10])[CH2:7][CH2:8][CH3:9].CS(C)=O>C(O)(=O)C>[C:6]([NH:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21]3[CH:22]=[CH:23][C:24](=[O:27])[NH:25][N:26]=3)[CH:18]=2)[CH2:13]1)(=[O:10])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 199728362-butyrylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indaneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 98176942-butyrylamino-5-[pyridazin-3(2H)-on-6-yl]indaneYield 88.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20 m of a 25% hydrogen bromide-acetic acid solution was added to 4.00 g of 2-butyrylamino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane suspended in 45 ml of acetic acid, and then 1.14 ml of dimethyl sulfoxide was added to the mixture. The resulting mixture was stirred at room temperature for 3.5 hours. Hydrogen bromide-acetic acid was removed, and the residue was recrystallized from hydrous ethanol to obtain 3.50 g of 2-butyrylamino-5-[pyridazin-3(2H)-on-6-yl]indane.

Workup

  1. customHydrogen bromide-acetic acid was removed
  2. customthe residue was recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-dac461ca3bbb4384a81f564fbc266676
Source dataset
uspto-grants-1996_08
Patent number
US05543409

Reaction notes

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