Ammonia → 1,1'-dithiobis[3-oxo-1,3-propanediyl]bis[2,3-dihydro-1H-indole-2-carboxylic acid]

HRID 434430Notes

Reaction equation

HRID 434430 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[C:23]([OH:25])=[O:24])=[O:13])(=O)C1C=CC=CC=1.[NH3:26]>O.C(OCC)(=O)C>[O:13]=[C:12]([N:26]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[C:23]([OH:25])=[O:24])[CH2:11][CH2:10][S:9][S:9][CH2:10][CH2:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[C:23]([OH:25])=[O:24])=[O:13]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 127642431-(3-Benzoylsulfanyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid

Product 1

HCID 127642631,1'-dithiobis[3-oxo-1,3-propanediyl]bis[2,3-dihydro-1H-indole-2-carboxylic acid]

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[3-(benzoylthio)-1-oxopropyl]-2,3-dihydro-1H-indole-2-carboxylic acid (3.0 g.) and methanolic ammonia (5.5 N solution, 45 ml.) was stirred at room temperature for 2.5 hours, then evaporated under reduced pressure on a rotary evaporator to give a resinous material. The residue was dissolved in water, and the aqueous solution was washed with ethyl acetate three times. The aqueous phase was acidified to pH ca. 2 by dropwise addition of dilute hydrochloric acid, whereby an oil separated. The oil was extracted with ethyl acetate (two times). The combined extract was washed with water, then with saline, and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated on a rotary evaporator under reduced pressure to give an oily residue which was placed under high vacuum to give a solid material. The crude product was dissolved in a small amount of warm ethyl acetate with warming on a steam bath (there was some insoluble solid material which was removed by filtration). The ethyl acetate solution was kept under mild nitrogen stream until a precipitate started to separate. The mixture was chilled in ice, then kept in a refrigerator. The precipitate was collected on a filter and washed with acetonitrile to give 1,1'-dithiobis[3-oxo-1,3-propanediyl]bis[2,3-dihydro-1H-indole-2-carboxylic acid], m.p. 213°-216°.

Workup

  1. customevaporated under reduced pressure on a rotary evaporator
  2. customto give a resinous material
  3. washthe aqueous solution was washed with ethyl acetate three times
  4. additionThe aqueous phase was acidified to pH ca. 2 by dropwise addition of dilute hydrochloric acid, whereby an oil
  5. customseparated
  6. extractionThe oil was extracted with ethyl acetate (two times)
  7. extractionThe combined extract
  8. washwas washed with water
  9. dry with materialwith saline, and dried over anhydrous sodium sulfate
  10. customThe ethyl acetate was evaporated on a rotary evaporator under reduced pressure
  11. customto give an oily residue which
  12. customto give a solid material
  13. temperaturewith warming on a steam bath (there
  14. customwas removed by filtration)
  15. customto separate
  16. temperatureThe mixture was chilled in ice
  17. customThe precipitate was collected on
  18. filtrationa filter
  19. washwashed with acetonitrile

Sources & evidence

ORD record
ord-0db48af57a224fb79b18642efd084371
Source dataset
uspto-grants-1983_08
Patent number
US04396773

Reaction notes

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