Water → 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1586537Notes

Reaction equation

HRID 1586537 reaction equation
OS([C:5]([F:8])([F:7])[F:6])(=O)=O.N[C:10]1O[C:13]([C:15](F)(F)F)=[N:12][C:11]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.ClC(=C)[C:28]#[N:29].C(OCC)(=O)C.O>CN(C)C=O.CCCCCCC>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:11]2[NH:12][C:13]([C:5]([F:8])([F:7])[F:6])=[CH:15][C:10]=2[C:28]#[N:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 701982-ChloroacrylonitrileHCID 15431063HCID 15431063, compound

Product 1

HCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

A solution of 5-amino-4-(p-chlorophenyl)-2-(trifluoromethyl)oxazole, triflate salt (16.5 g, 0.04 mol) in dimethylformamide is treated at 10° C. with 2-chloroacrylonitrile (5.25 g, 0.06 mol) under a nitrogen atmosphere, warmed to room temperature, held at room temperature for 4 hours, and treated with a mixture of ethyl acetate and water. The phases are separated and the organic phase is washed with water and concentrated to give a wet solid residue. Flash column chromatography on silica gel, packed with 15% ethyl acetate in heptane and eluted with 20% ethyl acetate in heptane of the residue gives, on crystallization from ethyl acetate/heptane, the title product as a pale yellow solid, 7.1 g (65% yield), mp 238.0°-241.0° C., identified by NMR analysis.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with water
  3. concentrationconcentrated
  4. customto give a wet solid residue
  5. washeluted with 20% ethyl acetate in heptane of the residue
  6. customgives, on crystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-3f781080becb4051b71ebc8868451f48
Source dataset
uspto-grants-1999_08
Patent number
US05945538

Reaction notes

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