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Hydrochloric Acid → Benzoic acid, 3-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]-

HRID 248694
Notes
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Reaction equation

HRID 248694 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:18]([S:21][CH2:22][CH:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24](Cl)=[O:25])(=[O:20])[CH3:19].Cl>C(Cl)(Cl)Cl.O>[C:18]([S:21][CH2:22][CH:23]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])=[O:25])(=[O:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 8471TriethylamineHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chloride

Product 1

HCID 10215552Benzoic acid, 3-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]-Yield 41.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6212ChloroformSolvent

Procedure

3-Aminobenzoic acid (1.4 g) is suspended in chloroform (50 ml), and thereto is added triethylamine (2.06 g), and to the mixture is added 2-acetylthiomethyl-3-phenylpropionyl chloride (2.61 g) with stirring under ice cooling, and the mixture is stirred for 30 minutes and further at room temperature three nights. To the reaction mixture is added water, and the mixture is acidified with hydrochloric acid and extracted with chloroform. The extract is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated under reduced pressure. The precipitates are separated by filtration and recrystallized from 50% aqueous ethanol to give the title compound (1.5 g).

Workup

  1. stirringthe mixture is stirred for 30 minutes and further at room temperature three nights
  2. extractionextracted with chloroform
  3. washThe extract is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  7. additionThe fractions containing the desired compound
  8. customare collected
  9. concentrationconcentrated under reduced pressure
  10. customThe precipitates are separated by filtration
  11. customrecrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-9086da73e5914ea48feda8ed24d0bab9
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05210266

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes