Ethanol → HCID 18929796, compound

HRID 1598573Notes

Reaction equation

HRID 1598573 reaction equation
I.[NH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=3)[CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[CH2:27]([S:31](Cl)(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30].C(O)C>CN1CCN(C)C1=O.C(OCC)(=O)C>[CH2:27]([S:31]([NH:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=3)[CH:9]=2)[CH2:4]1)(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 18929763HCID 18929763, compound

Product 1

HCID 18929796HCID 18929796, compound

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10.3 g of 2-amino-6-[4,5-dihydropyridazin-3(2H)-on-6-yl]-1,2,3,4-tetrahydronaphthalene.hydroiodide suspended in 100 ml of 1,3-dimethyl-2-imidazolidinone was added 26.7 ml of triethylamine at room temperature, and the mixture was stirred for 30 minutes. Under ice cooling, to the mixture was added dropwise 12.6 ml of butanesulfonyl chloride, and the mixture was stirred at room temperature for 4 hours. To the mixture was added 40 ml of ethanol, and the mixture was further stirred for 30 minutes. Ethyl acetate was added to the reaction mixture, the organic layer was washed with water and dried, and then the solvent was removed. The resulting crude crystals were recrystallized from isopropanol to obtain 8.5 g of 2-n-butylsulfonylamino-6-[4,5-dihydropyridazin-3(2H)-on-6-yl]-1,2,3,4-tetrahydronaphthalene.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. stirringthe mixture was further stirred for 30 minutes
  3. washthe organic layer was washed with water
  4. customdried
  5. customthe solvent was removed
  6. customThe resulting crude crystals were recrystallized from isopropanol

Sources & evidence

ORD record
ord-375c2353d9a5436088ff8d9c9049eb62
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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