Water → N-[4-Hydroxy-5-(4-fluorophenoxy)pentyl]-methanesulfonamide

HRID 973191Notes

Reaction equation

HRID 973191 reaction equation
[OH:1][CH:2]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH2:3][CH2:4][CH2:5][N:6](CCCCCCC(OCC)=O)[S:7]([CH3:10])(=[O:9])=[O:8].[OH-].[Na+].O>C(O)C>[OH:1][CH:2]([CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[CH2:3][CH2:4][CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21401586Ethyl 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}heptanoate

Product 1

HCID 86735163N-[4-Hydroxy-5-(4-fluorophenoxy)pentyl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of ethyl 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}heptanoate (4.7 g., 0.11 mole), sodium hydroxide (1.0 g.), water (13 ml.) and ethanol (130 ml.) is kept at room temperature for 20 hours. Most of the solvent is removed in vacuo, water (150 ml.) is added and the solution extracted with ether (100 ml.). The aqueous layer is acidified (hydrochloric acid) and extracted with ethyl acetate (2 × 100 ml.). The organic layer is dried over sodium sulfate then concentrated in vacuo to obtain the subject compound. The yield is 3.7 g. (84%) of heavy oil.

Workup

  1. customMost of the solvent is removed in vacuo, water (150 ml.)
  2. additionis added
  3. extractionthe solution extracted with ether (100 ml.)
  4. extractionextracted with ethyl acetate (2 × 100 ml.)
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customto obtain the subject compound

Sources & evidence

ORD record
ord-8aea0f1d361d4030aa76e40050d27a5d
Source dataset
uspto-grants-1977_10
Patent number
US04055596

Reaction notes

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