Propiolic Acid → 3-[(1H-Indol-3-yl)sulfanyl]prop-2-enoic acid

HRID 461631Notes

Reaction equation

HRID 461631 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[SH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1>[OH-].[Na+]>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([S:6][CH:3]=[CH:2][C:1]([OH:5])=[O:4])=[CH:8]1

Participants

4

Reactant 2

HCID 10110Propiolic AcidHCID 102001H-Indole-3-thiol

Product 1

HCID 544439283-[(1H-Indol-3-yl)sulfanyl]prop-2-enoic acidYield 80.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 35.0 g (0.5 mole) of propiolic acid, 97 g (0.5 mole) of 3-mercaptoindole and 500 ml of 1N NaOH solution is stirred for 1 hour at 95° C. The solution is cooled and the precipitated solid washed with water and discarded. The filtrate is acidified with 4N HCl and the gummy precipitate extracted with ether. The ether is dried and evaporated and the residue recrystallized from 250 ml of acetonitrile to give 88 g of product, mp 172°-173° C.

Workup

  1. temperatureThe solution is cooled
  2. washthe precipitated solid washed with water
  3. extractionthe gummy precipitate extracted with ether
  4. dry with materialThe ether is dried
  5. customevaporated
  6. customthe residue recrystallized from 250 ml of acetonitrile

Sources & evidence

ORD record
ord-aa51fc17db6c4242b488879b5773f65c
Source dataset
uspto-grants-1977_12
Patent number
US04064123

Reaction notes

Loading…