O-ethylhydroxylamine hydrochloride → 2-(1-(Ethoxyimino)propyl)-3-hydroxy-5-(4-(5-(methylsulfonyl)-2-pyridylthio)phenyl)cyclohex-2-en-1-one

HRID 703359Notes

Reaction equation

HRID 703359 reaction equation
[C:1]([C:5]1[C:6](=[O:29])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=3)=[CH:14][CH:13]=2)[CH2:9][C:10]=1[OH:11])(=O)[CH2:2][CH3:3].Cl.[CH2:31]([O:33][NH2:34])[CH3:32].C([O-])(=O)C.[Na+]>C(Cl)Cl.C(O)C>[CH2:31]([O:33][N:34]=[C:1]([C:5]1[C:6](=[O:29])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]([S:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][N:20]=3)=[CH:16][CH:17]=2)[CH2:9][C:10]=1[OH:11])[CH2:2][CH3:3])[CH3:32]

Participants

6

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458880HCID 178458880, compound

Product 1

HCID 1362094882-(1-(Ethoxyimino)propyl)-3-hydroxy-5-(4-(5-(methylsulfonyl)-2-pyridylthio)phenyl)cyclohex-2-en-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 4.60 g (0.0107 mol) of 2-propionyl-3-hydroxy-5-(4-(5-(methylsulfonyl)-2-pyridylthio)phenyl)cyclohex-2-en-1-one in 100 mL of methylene chloride and 100 mL of 95 percent ethanol was added 1.35 g (0.0139 mol) of ethoxyamine hydrochloride and 1.31 g (0.0160 mol) of anhydrous sodium acetate. The slurry was stirred at ambient temperature for 12 hours and diluted with 100 mL of methylene chloride and washed thrice with 150 mL portions of water. The organic layer was dried over sodium sulfate and the solvent was removed in vacuo leaving 4.8 g (94.7 percent of theoretical) of the crude product. The product was purified by column chromatography using 5:95 acetone:methylene chloride as eluent and then trituration with diethyl ether affording 2.60 g (51.3 percent of theoretical) of the above named title compound, melting at 125.5°-128.5° C.; 1H NMR (CDCl3): δ 1.05-1.40 (m, 6H, CH3CH2 -- and CH3CH2O--), 2.55-3.55 (m, 11H, ring protons, CH 3 SO2 --, CH3CH2 --), 4.10 (q, 2H, CH3CH2O--), 6.9-8.85 (m, 7H, ArH), 15.0 (broad s, br, 1H, OH).

Workup

  1. washwashed thrice with 150 mL portions of water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-434873ce9f4846399c90be03d89e0e7c
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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