Diethyl Ether → 1H-Pyrrole-3-carbonitrile, 4-(trifluoromethyl)-

HRID 1590572Notes

Reaction equation

HRID 1590572 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.[H-].[Na+].[CH:16](/[C:22]#[N:23])=[CH:17]\[C:18]([F:21])([F:20])[F:19].[CH2:24](OCC)C>CS(C)=O>[F:19][C:18]([F:21])([F:20])[C:17]1[C:16]([C:10]#[N:11])=[CH:22][NH:23][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 57087824,4,4-trifluorocrotononitrile

Product 1

HCID 151507031H-Pyrrole-3-carbonitrile, 4-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of p-tolylsulfonylmethylisocyanide (0.72 g, 3.2 mmol) and sodium hydride (0.09 g, 3.8 mmol) in anhydrous ethyl ether is treated dropwise with a solution of 4,4,4-trifluorocrotonitrile (0.38 g, 3.2 mmol) in ether and dimethyl sulfoxide over a 35 minute period, stirred at room temperature for 20 minutes and quenched with water. The phases are separated and the aqueous phase is extracted with ether. The organic phases are combined, washed with brine, dried over MgSO4 and concentrated in vacuo to afford an orange solid residue. The residue is flash chromatographed using silica gel and 100:100:1 petroleum ether: ethyl ether: acetic acid followed by 100% methylene chloride to give the title product as a white solid, mp 96°-97° C.

Workup

  1. customquenched with water
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ether
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford an orange solid residue
  8. customchromatographed

Sources & evidence

ORD record
ord-cc036325e0b04b4e8c9684add71e9318
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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