Sodium hydride → HCID 13324710, compound

HRID 544137Notes

Reaction equation

HRID 544137 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2.F[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]>CS(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678803-FluorobenzonitrileHCID 1175965-Chloroindoline

Product 1

HCID 13324710HCID 13324710, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A slurry of 2.64 g (0.11 mole, 1.1 equivalents) sodium hydride in 15.36 g (0.1 mole) 5-chloroindoline and 50 ml sieve dried DMSO was permitted to stir at room temperature under nitrogen for 2 hours. While cooling in an ice bath, a solution of 12.11 g (0.1 mole) 3-fluorobenzonitrile in 15 ml sieve dried DMSO was then added dropwise over 15 minutes. At the end of the addition, the ice bath was removed and the reaction mixture was permitted to warm to room temperature and stir overnight (20 hours). The product was poured onto ice and then extracted twice with CHCl3. The combined organic portions (400 ml) were washed four times with water (400 ml portions), 4 N HCl (three 300 ml portions) brine (300 ml), dried over Na2SO4, and concentrated to give 28.03 g (25.47 g theory) of a solid. Recrystallization from hot absolute ethanol containing 5-10% CHCl3 afforded 11.12 g (43.66% overall) of 3-(5-chloro-1-indolinyl)benzonitrile, m.p. 120°-121° C.

Workup

  1. temperatureWhile cooling in an ice bath
  2. additionAt the end of the addition
  3. customthe ice bath was removed
  4. temperatureto warm to room temperature
  5. stirringstir overnight (20 hours)
  6. additionThe product was poured onto ice
  7. extractionextracted twice with CHCl3
  8. washThe combined organic portions (400 ml) were washed four times with water (400 ml portions), 4 N HCl (three 300 ml portions) brine (300 ml)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customto give 28.03 g (25.47 g theory) of a solid
  12. customRecrystallization from hot absolute ethanol containing 5-10% CHCl3

Sources & evidence

ORD record
ord-8b6378c37e794827a4c24f3c97f3fc13
Source dataset
uspto-grants-1984_05
Patent number
US04448784

Reaction notes

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