Sodium Chloride → N-[3-Hydroxy-1-(pyridin-3-yl)propyl]-4-methylbenzene-1-sulfonamide

HRID 261094Notes

Reaction equation

HRID 261094 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][C:13](OCC)=[O:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Al+3].[Li+].[Cl-].[Na+]>C(COC)OC>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7]([NH:10][CH:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13][OH:14])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 53889535HCID 53889535, compound

Product 1

HCID 54438985N-[3-Hydroxy-1-(pyridin-3-yl)propyl]-4-methylbenzene-1-sulfonamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

89.7 g (0.26 mole) of the sulfonamide was added to a suspension of 12.7 g (0.34 mole) of lithium aluminum tetrahydride in 1250 ml of dry glyme. The mixture was stirred and heated under reflux for 1.5 hours. A saturated sodium chloride solution was added at a temperature of from 0° to 5° C. and the mixture stirred and heated under reflux for 30 additional minutes. The insolubles were removed by filtration after standing overnight and the cake was washed with 200 ml of boiling glyme followed by two 250 ml aliquots of ethyl alcohol. The pH was adjusted to 7.8 with sodium bicarbonate and hydrogen chloride. Most of the glyme and alcohol were removed under reduced pressure and the resulting solid collected, washed with water and dried in a desiccator to yield 75.6 g (95.5% yield) of 3-(p-toluenesulfonamido)-3-(3-pyridyl)propanol.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. stirringthe mixture stirred
  4. temperatureheated
  5. temperatureunder reflux for 30 additional minutes
  6. customThe insolubles were removed by filtration
  7. washthe cake was washed with 200 ml of boiling glyme
  8. customMost of the glyme and alcohol were removed under reduced pressure
  9. customthe resulting solid collected
  10. washwashed with water
  11. customdried in a desiccator

Sources & evidence

ORD record
ord-f95d24d22166423cb4371a70f0f966d8
Source dataset
uspto-grants-1979_08
Patent number
US04163855

Reaction notes

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