Dimethyl Sulfoxide → HCID 18977173, compound

HRID 2393740Notes

Reaction equation

HRID 2393740 reaction equation
Br.C(O)(=O)C.[CH:6]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=2)=[CH:17][CH:16]=1)(=[O:10])=[O:9])=[CH2:7].[CH3:28][S:29](C)=O>>[CH3:28][S:29][CH2:7][CH2:6][S:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24](=[O:27])[NH:25][N:26]=2)=[CH:17][CH:16]=1)(=[O:9])=[O:10]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 18977147HCID 18977147, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 18977173HCID 18977173, compoundYield 64.4%

Procedure

1.7 g of dimethylsulfoxide was added to a 25% hydrogen bromide-acetic acid suspension (50 ml) containing 5.30 g of 6-[4-(3-vinylsulfonylaminopropyl)phenyl]-4,5-dihydropyridazin-3(2H)-one, and the mixture was stirred at room temperature for 4.5 hours. After hydrogen bromide and acetic acid were removed, a 15% aqueous sodium methyl mercaptide solution (100 ml) was added to the residue, and the mixture was stirred at 60° C. for 1.5 hours. After cooling, the mixture was neutralized with hydrochloric acid, and crystal was collected by filtration, washed with water, dried and then recrystallized from acetonitrile to obtain 3.90 g of 6-[4-(3-(2-methylthioethyl)sulfonylaminopropyl)phenyl]pyridazin-3(2H)-one.

Workup

  1. customAfter hydrogen bromide and acetic acid were removed
  2. additiona 15% aqueous sodium methyl mercaptide solution (100 ml) was added to the residue
  3. stirringthe mixture was stirred at 60° C. for 1.5 hours
  4. temperatureAfter cooling
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-32f50fbf37ee47eb950b75c58cce37f1
Source dataset
uspto-grants-1998_09
Patent number
US05808065

Reaction notes

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