Dimethyl Sulfoxide → 4-Phenyl-1H-pyrrole-3-carbonitrile

HRID 1033580Notes

Reaction equation

HRID 1033580 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-])(=O)=O)=CC=1.[H-].[Na+].[CH3:26]S(C)=O>CCOCC.O>[C:4]1([C:3]2[C:2]([C:20]#[N:21])=[CH:1][NH:10][CH:26]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 746673-Phenylprop-2-enenitrileHCID 161915Tosylmethyl isocyanide

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a mixture of 5.0 g (39 mmol) of cinnamonitrile and 7.6 g (39 mmol) of (p-tolylsulfonyl)methyl isocyanide in 35 mL of DMSO and 65 mL of ether is added over a 20 minute period a suspension of 1.86 g of a 60% oil suspension of sodium hydride (1.11 g; 46 mmol) in 80 mL of ether. The reaction mixture is maintained under nitrogen for an hour and then diluted with ether and water. The ether layer is separated, dried over magnesium sulfate, and concentrated in vacuo. The resulting oil is chromatographed on silica gel using 1:1 chloroform ethyl acetate to give 2.5 g of cream-colored solids. Recrystallization from ether-hexane affords 1.15 g, m.p. 123°-125° C.; NMR M86-1077.

Workup

  1. additionis added over a 20 minute period
  2. temperatureThe reaction mixture is maintained under nitrogen for an hour
  3. customThe ether layer is separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil is chromatographed on silica gel using 1:1 chloroform ethyl acetate

Sources & evidence

ORD record
ord-ce8ccdb25c9e4f8f8cdf3cbf6b9f71b8
Source dataset
uspto-grants-1994_05
Patent number
US05310938

Reaction notes

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