Acrylic Acid → 3-(2-Indolylthio)Propionic Acid

HRID 1086514Notes

Reaction equation

HRID 1086514 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[S:10].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13]>C(N(CC)CC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][CH2:13][CH2:12][C:11]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 30323102-Indolinethione

Product 1

HCID 151627253-(2-Indolylthio)Propionic Acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

One liter of triethylamine is added slowly in the course of 2 hours 30 minutes to a vigorously stirred suspension of 194 g (1.3 mol) of 2-indolinethione (prepared according to Y. Nakisumi and Coll. Chem. Pharm. Bull. 1984, 32, (3), 877) in 108 g (1.5 mol) of acrylic acid. The mixture is brought to reflux for 12 hours while stirring is maintained, and then cooled and concentrated under vacuum. The residue is taken up with 10% strength aqueous sodium bicarbonate solution and the mixture is filtered. The filtrate is acidified with aqueous hydrochloric acid solution. The precipitate formed is drained, washed with water and dried. It is recrystallized in toluene.

Workup

  1. temperatureto reflux for 12 hours
  2. temperatureis maintained
  3. temperaturecooled
  4. concentrationconcentrated under vacuum
  5. filtrationthe mixture is filtered
  6. customThe precipitate formed
  7. washwashed with water
  8. customdried
  9. customIt is recrystallized in toluene

Sources & evidence

ORD record
ord-20cb8c442e4947de94098163c8963863
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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