Sodium Hydroxide → 2-[1-(2,4-Dichlorophenyl)vinyl]indole

HRID 373997Notes

Reaction equation

HRID 373997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:12](S(C2C=CC=CC=2)(=O)=O)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:10].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 198088442-[1-(2,4-Dichlorophenyl)vinyl]-1-phenylsulfonylindole

Product 1

HCID 198087192-[1-(2,4-Dichlorophenyl)vinyl]indoleYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol was dissolved 2.5 g of 2-[1-(2,4-dichlorophenyl)vinyl]-1-phenylsulfonylindole. Thereto was added 20 ml of a 5 N aqueous sodium hydroxide solution. The mixture was refluxed for 20 hours. The solvent was removed by distillation under reduced pressure. The residue was mixed with 20 ml of water. The mixture was adjusted to pH 7.0 with diluted hydrochloric acid, and extracted with 100 ml of ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.5 g of 2-[1-(2,4-dichlorophenyl)vinyl]indole as a light yellow oily material.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionThe residue was mixed with 20 ml of water
  4. extractionextracted with 100 ml of ethyl acetate
  5. washThe extract was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0214ed60632a4fc089fada0ef2e6ee27
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…