HCID 12764242, compound → 1-(3-Benzoylsulfanyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid

HRID 1262906Notes

Reaction equation

HRID 1262906 reaction equation
[O:1]=[C:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:14]([OH:16])=[O:15])[CH:3]=[CH2:4].[C:17]([OH:25])(=[S:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[C:17]([S:24][CH2:4][CH2:3][C:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:14]([OH:16])=[O:15])=[O:1])(=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 12764242HCID 12764242, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 127642431-(3-Benzoylsulfanyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring mixture of 2,3-dihydro-1-(1-oxo-2-propenyl)-1H-indole-2-carboxylic acid (6.52 g.) and methylene chloride 160 ml.) was added dropwise thiobenzoic acid (95%, 4.36 g.) dissolved in a small amount of methylene chloride. During the addition, the reaction mixture was chilled in ice. The ice bath was removed in 10 minutes after the completion of the addition, but the stirring was continued for 1 hour. The reaction mixture was then immersed in an oil bath maintained at 80° for 2.5 hours. The reaction mixture was concentrated on a rotary evaporator under reduced pressure to ca. 30 ml., and kept in a refrigerator for 1 day. A precipitate was collected on a filter and washed with methylene chloride to give the titled compound which melted at 173°-175°, and weighed 11.0 g.

Workup

  1. additionDuring the addition
  2. temperaturethe reaction mixture was chilled in ice
  3. customThe ice bath was removed in 10 minutes
  4. additionafter the completion of the addition
  5. customThe reaction mixture was then immersed in an oil bath
  6. temperaturemaintained at 80° for 2.5 hours
  7. concentrationThe reaction mixture was concentrated on a rotary evaporator under reduced pressure to ca. 30 ml
  8. wait, and kept in a refrigerator for 1 day
  9. customA precipitate was collected on
  10. filtrationa filter
  11. washwashed with methylene chloride

Sources & evidence

ORD record
ord-40bdc9c650464706961d351bd4e16c82
Source dataset
uspto-grants-1984_06
Patent number
US04454292

Reaction notes

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