Indole → HCID 11806153, compound

HRID 544139Notes

Reaction equation

HRID 544139 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[H][H].F[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]>CS(C)=O>[N:1]1([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 798IndoleHCID 24758Sodium hydrideHCID 678803-FluorobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 11806153HCID 11806153, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution, under nitrogen, of 17.6 g (0.150 mole) of indole in 100 ml of dry dimethylsulfoxide (DMSO) was added 4.5 g (0.188 mole) of sodium hydride in portions over a 1.5 hour period. When no more bubbles of hydrogen were visible (4-5 hours), there was added dropwise a solution of 22.8 g (0.188 mole) of 3-fluorobenzonitrile in 25 ml of dry DMSO. When the addition was complete (1 hour) the mixture was stirred overnight (about 16 hours) and then 3 hours at 100° C. The cooled mixture was poured into 1.5 liters of a stirred water-ice mixture to precipitate a semi-solid. The supernatent was poured off and the coagulated material was washed several times more with water. It was then dissolved in 500 ml of dichloromethane, washed twice with dilute brine, dried over Na2SO4, and concentrated in vacuo to an oil. This material weighed 32 g (100% yield). A portion was distilled yielding 3-(1-indolyl)benzonitrile (160°/0.1 mm) in 75% overall yield. The product was a soft, crystalline material at room temperature, m.p. 33°-36° C.

Workup

  1. custom(4-5 hours), there
  2. additionWhen the addition
  3. custom(1 hour)
  4. custom3 hours
  5. customat 100° C
  6. customto precipitate a semi-solid
  7. additionThe supernatent was poured off
  8. washthe coagulated material was washed several times more with water
  9. dissolutionIt was then dissolved in 500 ml of dichloromethane
  10. washwashed twice with dilute brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated in vacuo to an oil
  13. distillationA portion was distilled

Sources & evidence

ORD record
ord-9a544fbc0c5142c69d7d5802d30c4ef7
Source dataset
uspto-grants-1984_05
Patent number
US04448784

Reaction notes

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