Hydrochloric Acid → HCID 18950657, compound

HRID 1492565Notes

Reaction equation

HRID 1492565 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH2:18][CH:19]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]COC)=[CH:23][CH:22]=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>CO>[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH2:18][CH:19]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18950741HCID 18950741, compound

Product 1

HCID 18950657HCID 18950657, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In argon atmosphere, 0.54 g of N-ethoxycarbonyl-N-[4-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)butyl]-4-chlorobenzene sulfonamide was dissolved in 15 ml of methanol, followed by addition of 1 ml of 6N hydrogen chloride, and stirred at 60 ° C. for 45 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure, followed by addition of methylene chloride and further by addition of saturated aqueous sodium hydrogencarbonate so that the resulting mixture became weak alkaline. The organic phase was separated, which was then extracted with methylene chloride. The organic phases combined were washed in saturated aqueous sodium chloride and dried over magnesium sulfate. After the evaporation of the solvent, 0.47 g of N-ethoxycarbonyl-N-[4-(4-hydroxyphenyl)-3-(3-pyridyl)butyl]-4-chlorobenzenesulfonamide was produced.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionfollowed by addition of methylene chloride and further by addition of saturated aqueous sodium hydrogencarbonate so that the resulting mixture
  4. customThe organic phase was separated
  5. extractionwhich was then extracted with methylene chloride
  6. washThe organic phases combined were washed in saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customAfter the evaporation of the solvent

Sources & evidence

ORD record
ord-b6e2753310044fc5a95bb31d7a65408d
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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