Hydrochloric Acid → HCID 18950758, compound

HRID 1492542Notes

Reaction equation

HRID 1492542 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH:18]([C:26]1[CH:31]=[CH:30][C:29]([O:32]COC)=[CH:28][CH:27]=1)[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[S:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5])[CH3:2].Cl.O.C(=O)([O-])O.[Na+]>O1CCOCC1.C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH:18]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[S:7]([C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)(=[O:9])=[O:8])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 18950737HCID 18950737, compound

Product 1

HCID 18950758HCID 18950758, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To the solution of 8 ml of the solution of 1.11 g of N-ethoxycarbonyl-N-[2-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide in dioxane was added 2 ml of aqueous 6N hydrogen chloride solution, and stirred at room temperature for 7 hours. To the reaction mixture were added water and methylene chloride, followed by further addition of sodium hydrogen carbonate. The organic phase was separated, which was then extracted with ethyl acetate from aqueous phase. The organic phases were combined and washed in saturated aqueous sodium chloride, followed by drying over magnesium sulfate to distill off the solvent under reduced pressure. The obtained residue was subjected to chromatography on a silica gel column, and from the fraction eluted with methanol-methylene chloride (1:99 v/v) was obtained 956 mg of N-ethoxycarbonyl-N-[2-(4-hydroxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide.

Workup

  1. customThe organic phase was separated
  2. extractionwhich was then extracted with ethyl acetate from aqueous phase
  3. washwashed in saturated aqueous sodium chloride
  4. dry with materialby drying over magnesium sulfate
  5. distillationto distill off the solvent under reduced pressure
  6. washfrom the fraction eluted with methanol-methylene chloride (1:99 v/v)

Sources & evidence

ORD record
ord-44828ae1e17d4b689f21db8afbe885b6
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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