Sodium hydride → 4-Phenyl-1H-pyrrole-3-carbonitrile

HRID 1765613Notes

Reaction equation

HRID 1765613 reaction equation
[C:1](#[N:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=1.[H-].[Na+]>CCOCC.CS(C)=O.O>[C:1]([C:2]1[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:22][NH:21][CH:20]=1)#[N:10]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 746673-Phenylprop-2-enenitrileHCID 161915Tosylmethyl isocyanide

Product 1

HCID 37214604-Phenyl-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of cinnamonitrile (16.53 g) and (para-toluenesulfonyl)methylisocyanide (25 g) in a mixture of ether and dimethyl sulphoxide (450 mL, 2:1) was added dropwise to a stirred suspension of sodium hydride (6.14 g, 60% dispersion in mineral oil) in ether (50 mL). An exothermic reaction took place. The reaction mixture was then stirred at room temperature for 2 hours, then diluted with water (500 mL) and this mixture was extracted three times with ether (250 mL). The combined extracts were washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to filter chromatography on a pad of silica eluting with a mixture of ethyl acetate and pentane (1L, 1:4, v/v) and then with a mixture of ethyl acetate and pentane (2L, 2:3, v/v). Fractions containing the required material were evaporated and the residue was suspended in pentane (500 mL) with stirring, then filtered to give the title compound as a solid, m.p. 120–122° C. MS: 167 (MH−).

Workup

  1. customAn exothermic reaction
  2. extractionthis mixture was extracted three times with ether (250 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. filtrationto filter chromatography on a pad of silica eluting
  7. additionwith a mixture of ethyl acetate and pentane (1L, 1:4, v/v)
  8. additionwith a mixture of ethyl acetate and pentane (2L, 2:3
  9. additionFractions containing the required material
  10. customwere evaporated
  11. stirringwith stirring
  12. filtrationfiltered

Sources & evidence

ORD record
ord-a8d6d8f9e02447628394cbedb66f8aed
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

Loading…