Benzyl Chloride → 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1-(phenylmethyl)-1H-indole-5-carbonitrile

HRID 1414035Notes

Reaction equation

HRID 1414035 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=2)[NH:18][CH:17]=1.[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O.O>[O:13]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:3])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=2)[N:18]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 103809773-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

Product 1

HCID 202894513-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1-(phenylmethyl)-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.16 g) was added to a solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-carbonitrile (2.0 g) in dry dimethylformamide (40 ml) under nitrogen. After 0.5 hour. benzyl chloride was added and after a further 2 hours the mixture was diluted with water (150 ml) and extracted with ethyl acetate (3×40 ml). Evaporation of the washed (H2O) and dried (MgSO4) extract gave a red oil which was triturated with ether and then crystallised from ethanol to give the title compound as yellow microcrystals (1.2 g) m.p. 182°-4° C. T.L.C. Silica, ether Rf 0.45.

Workup

  1. extractionextracted with ethyl acetate (3×40 ml)
  2. customEvaporation of the
  3. washwashed (H2O)
  4. dry with materialdried (MgSO4)
  5. extractionextract
  6. customgave a red oil which
  7. customwas triturated with ether
  8. customcrystallised from ethanol

Sources & evidence

ORD record
ord-51ae916885e24bfc8c91eb9af8fcbe92
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

Loading…