Propionic Acid → HCID 18349624, compound

HRID 378638Notes

Reaction equation

HRID 378638 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[NH2:9][C:10]([CH3:14])([CH3:13])[CH2:11]O.C1(C)C=CC=CC=1.[C:22](O)(=[O:25])[CH2:23][CH3:24]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:11][C:10]([NH:9][C:22](=[O:25])[CH2:23][CH3:24])([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 1140TolueneHCID 7815p-ChlorothiophenolHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 18349624HCID 18349624, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chlorothiophenol (64.8 g), 2-amino-2-methylpropanol (39.8 g) and toluene (160 ml) was treated with propionic acid (33.2 g) and the mixture boiled under reflux for 24 hours, collecting the water formed using a Dean and Stark apparatus. The mixture was dissolved in dichloromethane, washed with saturated sodium bicarbonate solution, dilute sodium hydroxide solution and then water. The organic layer was dried, filtered and evaporated to give an oil which was dried under high vacuum at 70° C. The oil, which solidified on standing, was dissolved in ether and treated with ethereal hydrogen chloride to give N-[2-(4-chlorophenylthio)-1,1-dimethylethyl]propionamide.

Workup

  1. temperatureunder reflux for 24 hours
  2. customcollecting the water
  3. customformed
  4. washwashed with saturated sodium bicarbonate solution, dilute sodium hydroxide solution
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil which
  9. customwas dried under high vacuum at 70° C
  10. dissolutionwas dissolved in ether
  11. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-579817a6d2be40308a6e87497e9078aa
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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