Beta-Alanine → HCID 86733766, compound

HRID 918582Notes

Reaction equation

HRID 918582 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].Br[CH:8]([CH3:12])[C:9](Cl)=[O:10].[C:13]([OH:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+]>O.C(N(CC)CC)C>[C:13]([S:20][CH:8]([CH3:12])[C:9]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:10])(=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 14797Potassium HydroxideHCID 979802-Bromopropanoyl chlorideHCID 178526132HCID 178526132, compound

Product 1

HCID 86733766HCID 86733766, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

8.9g (0.10 mol) of β-alanine was dissolved in 100 ml of water. To the solution was added 20 ml of triethylamine and then was added dropwise 22.2g (0.13 mol) of 2-bromopropionylchloride over one hour while stirring and ice-cooling. The mixture was stirred for a further 2 hours. To the mixture was added the filtrate which had been prepared by neutralizing 19.5g (0.14 mol) of thiobenzoic acid with an aqueous KOH and filtering the solution, followed by stirring overnight. Crystals precipitated were recovered by filtration, washed with water and dried to give 20.8g of N-(2-benzoylmercaptopropionyl-β-alanine. After recrystallization from benzene, the product had a melting point of 94° - 97°C.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred for a further 2 hours
  3. additionTo the mixture was added the filtrate which
  4. filtrationfiltering the solution
  5. stirringby stirring overnight
  6. customCrystals precipitated
  7. filtrationwere recovered by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-be8c00eb578840998e24f8c318c3868f
Source dataset
uspto-grants-1976_07
Patent number
US03971828

Reaction notes

Loading…