3,4-dihydro-2H-pyran → N-[[4-[2-(5-hydroxypentylidene)hydrazinyl]phenyl]methyl]methanesulfonamide

HRID 1647784Notes

Reaction equation

HRID 1647784 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1)[NH2:3].C([O-])(=O)C.[Na+].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>O.C(O)C>[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[N:3][NH:2][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 517045Sodium AcetateHCID 19921668N-[(4-hydrazinylphenyl)methyl]methanesulfonamide hydrochloride

Product 1

HCID 69011933N-[[4-[2-(5-hydroxypentylidene)hydrazinyl]phenyl]methyl]methanesulfonamideYield 39.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 23.9 g of crude N-[(4-hydrazinylphenyl)methyl]methanesulfonamide hydrochloride in 175 mL of water and 300 mL of ethanol was added sufficient sodium acetate to bring the pH to 4. To the resulting suspension was added 10.4 mL (114 mmol, 1.3 equiv.) of 3,4- dihydro-2H-pyran. The mixture was then stirred for twenty hours at room temperature. The ethanol was removed in vacuo. The pH was raised to 10 by adding solid potassium carbonate and the mixture was extracted three times with 50 mL portions of methylene chloride. The combined organic layers were washed with 25 mL of saturated aqueous sodium chloride, dried over magnesium sulfate and filtered to give an oil. The oil was purified by chromatography on silica gel using 5% methanol in methylene chloride containing 0.5% concentrated aqueous ammonium hydroxide to yield 11.1 g (39%, two steps) of pure N-[[4-[2-(5-hydroxypentylidene)hydrazinyl]phenyl]methyl]methanesulfonamide.

Workup

  1. customThe ethanol was removed in vacuo
  2. temperatureThe pH was raised to 10
  3. additionby adding solid potassium carbonate
  4. extractionthe mixture was extracted three times with 50 mL portions of methylene chloride
  5. washThe combined organic layers were washed with 25 mL of saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customto give an oil
  9. customThe oil was purified by chromatography on silica gel using 5% methanol in methylene chloride containing 0.5% concentrated aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-4ce862762426456c8cc15ff68981ce2d
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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