Water → 5-cyano-N-[2-(2'-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

HRID 1351783Notes

Reaction equation

HRID 1351783 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:33][CH3:34])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3SC)=[CH:17][C:16]=2[O:29][CH2:30][O:31][CH3:32])(=O)=[O:10])[CH:8]=1)#[N:2].[C:35](=O)(O)[O-].[Na+].O[O:41][S:42]([O-:44])=O.[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].[OH2:53]>CC(C)=O.C(OCC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:33][CH3:34])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:42]([CH3:35])(=[O:44])=[O:41])=[CH:17][C:16]=2[O:29][CH2:30][O:31][CH3:32])(=[O:10])=[O:53])[CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 962Water2×HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 178562315-cyano-2-methoxy-N-[2-(3-methoxymethoxy-2'-methylthiobiphenyl-4-yl)ethyl]benzenesulfonamideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 178562285-cyano-N-[2-(2'-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 26.44 g of 5-cyano-2-methoxy-N-[2-(3-methoxymethoxy-2′-methylthiobiphenyl-4-yl)ethyl]-benzenesulfonamide and 35.6 g of sodium bicarbonate in a mixture of 530 mL of acetone and 106 mL of water was added two portions of 81.5 g of OXONE (trademark) every 15 minutes under ice-cooling. The mixture was stirred under the same condition for 3 hours, and 100 mL of diethylether, 100 mL of water, and saturated aqueous sodium sulfate solution were added to the stirred reaction mixture under ice-cooling. The obtained mixture was concentrated under reduced pressure to remove acetone, and 300 mL of water, and diethyl ether-hexane were added to the stirred residue under ice-cooling. The mixture was stirred for 30 minutes, and the precipitate was collected by filtration, washed with water and diethyl ether-hexane to give 27.1 g of 5-cyano-N-[2-(2′-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide as a white powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationThe obtained mixture was concentrated under reduced pressure
  4. customto remove acetone, and 300 mL of water, and diethyl ether-hexane
  5. additionwere added to the stirred residue under ice-
  6. temperaturecooling
  7. stirringThe mixture was stirred for 30 minutes
  8. filtrationthe precipitate was collected by filtration
  9. washwashed with water and diethyl ether-hexane

Sources & evidence

ORD record
ord-953d03848cff45f1adb1f070d2904df2
Source dataset
uspto-grants-2007_05
Patent number
US07217832B2

Reaction notes

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