Hydrochloric Acid → N-[1-(Mercaptomethyl)-2-phenylethyl]benzamide

HRID 1856409Notes

Reaction equation

HRID 1856409 reaction equation
[C:1]1([CH2:7][CH:8]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC(N)=[S:22].[OH-].[Na+].Cl>C(O)C.O>[C:1]1([CH2:7][CH:8]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][SH:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 209006Benzamide, N-(alpha-(chloromethyl)phenethyl)-HCID 2723790Thiourea

Product 1

HCID 23344907N-[1-(Mercaptomethyl)-2-phenylethyl]benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

80.4 millimole (mm) of 3-phenyl-2-benzamido-1-chloropropane and 80.4 mm of thiourea are dissolved in 300 ml of ethanol. The resulting solution is refluxed for three hours. 6.7 g of sodium hydroxide is dissolved in 40 ml of water and is added under an inert atmosphere to the solution which is thereafter refluxed for an additional 21/2 hours. The solution is then cooled and acidified to pH 1 with 1 N HCl. The resulting mixture is then poured over ice to yield a precipitate which is collected by filtration and then dissolved in chloroform. The chloroform is dried with magnesium sulfate and then evaporated to yield the solid 3-phenyl-2-benzamido-1-propanethiol.

Workup

  1. temperatureThe resulting solution is refluxed for three hours
  2. additionis added under an inert atmosphere to the solution which
  3. temperatureis thereafter refluxed for an additional 21/2 hours
  4. temperatureThe solution is then cooled
  5. additionThe resulting mixture is then poured over ice
  6. customto yield a precipitate which
  7. filtrationis collected by filtration
  8. dissolutiondissolved in chloroform
  9. dry with materialThe chloroform is dried with magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-04a9c60c17ad4dd0a7e2682609dd8f0f
Source dataset
uspto-grants-1980_08
Patent number
US04219497

Reaction notes

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