Thionyl Chloride → HCID 19028810, compound

HRID 129226Notes

Reaction equation

HRID 129226 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][CH2:29][C:30](O)=[O:31])=[CH:20]1)(=[O:18])=[O:17])([CH3:3])[CH3:2].S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:7]=[C:6]([CH:13]([CH3:14])[CH3:15])[C:5]=1[S:16]([N:19]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:30](=[O:31])[CH2:29][CH2:28][C:21]([C:22]=23)=[CH:20]1)(=[O:17])=[O:18])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15542697HCID 15542697, compound

Product 1

HCID 19028810HCID 19028810, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(2,4,6-triisopropylphenylsulfonyl)-indole-3-propionic acid (76.22 g) in chloroform (500 ml) was added dropwise thionyl chloride (28.9 ml) at room temperature taking about 10 minutes. The mixture was stirred for one hour at 60° C. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was again added chloroform, followed by concentration under reduced pressure. The concentrate was dissolved in dichloroethane (900 ml). To the solution was gradually added, under ice-cooling, crushed aluminum chloride (58.4 g). The mixture was stirred for 30 minutes, and was added to a mixture of 1N hydrochloric acid (1000 ml) and ice (200 g), followed by extraction with chloroform (900 ml). The extract solution was washed with water (900 ml), dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure. The concentrate was purified by means of a column chromatography (eluted with ethyl acetate:n-hexane=1:4), followed by recrystallization from ethyl acetate-hexane to afford the title compound (43.86 g, m.p.124°-130° C.).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. concentrationfollowed by concentration under reduced pressure
  4. dissolutionThe concentrate was dissolved in dichloroethane (900 ml)
  5. additionTo the solution was gradually added, under ice-
  6. temperaturecooling
  7. customcrushed aluminum chloride (58.4 g)
  8. stirringThe mixture was stirred for 30 minutes
  9. additionwas added to a mixture of 1N hydrochloric acid (1000 ml) and ice (200 g)
  10. extractionfollowed by extraction with chloroform (900 ml)
  11. washThe extract solution was washed with water (900 ml)
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationwas concentrated under reduced pressure
  14. customThe concentrate was purified by means of a column chromatography (eluted with ethyl acetate:n-hexane=1:4)
  15. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cd545fd8b3504818961875a3de8848c4
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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