Dimethyl Sulfoxide → HCID 12764242, compound

HRID 851546Notes

Reaction equation

HRID 851546 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15](=[O:18])[CH:16]=[CH2:17])=[O:5])C.CS(C)=O.[OH-].[K+]>O.[OH-].[Na+]>[O:18]=[C:15]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:6]1[C:4]([OH:5])=[O:3])[CH:16]=[CH2:17]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 128420392,3-Dihydro-1-(1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 12764242HCID 12764242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,3-dihydro-1-(1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester (14.4 g.), 80% aqueous dimethyl-sulfoxide (200 ml.) and potassium hydroxide (86% pellets, 3.83 g.) was stirred under nitrogen atmosphere for 2.5 days at room temperature, then evaporated under reduced pressure on a rotary evaporator to give an oily residue. The residue was dissolved in water with the aide of a small amount of dilute sodium hydroxide solution. The aqueous solution was washed with ether twice, then made acidic by addition of dilute hydrochloric acid to pH ca. 2. The oil thus separated was extracted with ether three times. The combined ether extract was washed with water, then with saline, and dried over anhydrous magnesium sulfate. Evaporation of the ether on a rotary evaporator under reduced pressure gave a solid residue which melted at 158°-160°, and weighed 9.2 g. Recrystallization from ethyl acetate improved the melting point to 167°-169°.

Workup

  1. customevaporated under reduced pressure on a rotary evaporator
  2. customto give an oily residue
  3. washThe aqueous solution was washed with ether twice
  4. additionmade acidic by addition of dilute hydrochloric acid to pH ca. 2
  5. customThe oil thus separated
  6. extractionwas extracted with ether three times
  7. extractionThe combined ether extract
  8. washwas washed with water
  9. dry with materialwith saline, and dried over anhydrous magnesium sulfate
  10. customEvaporation of the ether
  11. customon a rotary evaporator under reduced pressure
  12. customgave a solid residue which melted at 158°-160°
  13. customRecrystallization from ethyl acetate
  14. customto 167°-169°

Sources & evidence

ORD record
ord-cdc954d39516418a9f1a924c8a1d37b2
Source dataset
uspto-grants-1983_05
Patent number
US04385180

Reaction notes

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