Hydrochloric Acid → HCID 18950693, compound

HRID 1492516Notes

Reaction equation

HRID 1492516 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][C:29]([O:32]COC)=[CH:28][CH:27]=1)[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>C(O)C>[CH2:1]([O:3][C:4]([N:6]([CH2:17][CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18950734HCID 18950734, compound

Product 1

HCID 18950693HCID 18950693, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 1.03 g portion of the thus obtained N-ethoxycarbonyl-N-[3-(4 -methoxymethyloxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide was dissolved in 25 ml of ethanol. After adding 1 ml of 6N hydrochloric acid, the solution was stirred at 60° C. for 1.5 hours. The resulting reaction mixture was concentrated under a reduced pressure, mixed with methylene chloride and then adjusted to alkalinity with saturated sodium hydrogencarbonate aqueous solution to separate organic layer. After extraction with chloroform, the extract was washed with saturated sodium chloride aqueous solution and dried using anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under a reduced pressure to obtain 0.80 g of N-ethoxycarbonyl-N-[3-(4-hydroxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzene sulfonamide.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under a reduced pressure
  3. additionmixed with methylene chloride
  4. customto separate organic layer
  5. extractionAfter extraction with chloroform
  6. washthe extract was washed with saturated sodium chloride aqueous solution
  7. customdried
  8. customThereafter, the solvent was removed by distillation under a reduced pressure

Sources & evidence

ORD record
ord-fb9880ab5a0a4a02aeb190cd50dee298
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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