Water → HCID 23470789, compound

HRID 127929Notes

Reaction equation

HRID 127929 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl[CH2:16][CH2:17][CH2:18][OH:19]>COCCOC>[C:7]([NH:6][C:5]1[CH:10]=[CH:11][C:2]([S:1][CH2:16][CH2:17][CH2:18][OH:19])=[CH:3][CH:4]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 123133-Chloro-1-propanolHCID 14798Sodium HydroxideHCID 707774'-Mercaptoacetanilide

Product 1

HCID 23470789HCID 23470789, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 16.7 g (0.1 mole) of p-mercaptoacetanilide, 4 g of sodium hydroxide, 40 ml of water, 40 ml of 1,2-dimethoxyethane, and 0.39 g (0.11 mole) of 3-chloropropanol is heated in a steam bath with stirring for 30 minutes. Two liquid phases are formed, and TLC indicates that the reaction is substantially complete. The mixture is distilled in vacuo to remove 1,2-dimethoxyethane, and the oily mixture which separates is triturated with cold water until it solidifies. The crude product is recrystallized from ethanol to obtain a by-product: the disulfide derived from the starting mercapto compound. The ethanol filtrate is concentrated, and the residue is triturated with ether-hexane to obtain 15.7 g of the desired product. Recrystallization from ethyl acetate-hexane gives 11.8 g of 3-(p-acetamidophenylthio)propanol which shows the correct IR and NMR spectra.

Workup

  1. temperatureis heated in a steam bath
  2. customTwo liquid phases are formed
  3. distillationThe mixture is distilled in vacuo
  4. customto remove 1,2-dimethoxyethane
  5. customthe oily mixture which separates is triturated with cold water until it
  6. customThe crude product is recrystallized from ethanol
  7. customto obtain a by-product
  8. concentrationThe ethanol filtrate is concentrated
  9. customthe residue is triturated with ether-hexane

Sources & evidence

ORD record
ord-2a2c6b947b7e46ceb2ef57487bb28722
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

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