Methanesulfonic Acid → 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1290227Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]([N:9]([CH3:16])[C:10](=O)[C:11]([F:14])([F:13])[F:12])[C:7]#N)=[CH:4][CH:3]=1.ClC(=C)[C:21]#[N:22].[CH3:24]S(O)(=O)=O.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[N:9]([CH3:16])[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:24][C:7]=2[C:21]#[N:22])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of N-(p-chloro-a-cyanobenzyl)-2,2,2-trifluoro-N-methylacetamide (13.8 g, 0.05 mol) in toluene is treated with 2-chloroacrylonitrile (4.4 g, 0.05 mol) and methanesulfonic acid (4.8 g, 0.05 mol), heated at 110° C. for 4 hours, treated with a second portion of 2-chloroacrylonitrile (4.4 g, 0.05 mol) and methanesulfonic acid (4.8 g, 0.05 mol), heated at 110° C. for 12 hours, cooled and treated with ethyl acetate and water. The phases are separated and the organic phase is washed with water and concentrated to give a residue. The residue is chromatographed using silica gel packed with 15% ethyl acetate in heptane and eluted with 20% ethyl acetate in heptane to give the title product as pale yellow crystals, 4.8 g (34% yield), mp 129°-130° C.

Workup

temperatureheated at 110° C. for 12 hours
temperaturecooled
customThe phases are separated
washthe organic phase is washed with water
concentrationconcentrated
customto give a residue
customThe residue is chromatographed
washeluted with 20% ethyl acetate in heptane

Sources & evidence

ORD record: ord-16f5559ac0f5458b848baaf4db403dfa
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750726

Reaction notes

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