Acetyl chloride → 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]#N)[NH:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.CS(O)(=O)=O.C(Cl)(=O)C.ClC(=C)[C:29]#[N:30].[CH2:32](N(CC)CC)C>C1(C)C=CC=CC=1.C(#N)C.O.CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([C:11]([F:12])([F:13])[F:14])=[CH:32][C:16]=2[C:29]#[N:30])=[CH:6][CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 80 °C
Procedure
A slurry of N-[(p-chlorophenyl)cyanomethyl]-2,2,2-trifluoroacetamide (13.1 g, 0.05 mol) in toluene is treated sequentially with methanesulfonic acid (2.4 g, 0.025 mol) and acetyl chloride (4.32 g, 0.055 mol), at room temperature, heated at 80° C. for 2 hours, cooled to room temperature, diluted with acetonitrile, treated first with 2-chloroacrylonitrile (5.25 g, 0.06 mol) then dropwise with triethylamine (13.7 g, 0.135 mol), heated at 70°-72° C. for 1 hour, cooled to room temperature and diluted with water. The mixture is extracted with ethyl acetate. The extracts are combined, washed with water and concentrated in vacuo to give a residue. Flash chromatography (silica-gel; 15% ethyl acetate in heptane as eluent) to give the title product.
Workup
- temperaturecooled to room temperature
- temperaturecooled to room temperature
- extractionThe mixture is extracted with ethyl acetate
- washwashed with water
- concentrationconcentrated in vacuo
- customto give a residue
Sources & evidence
- ORD record
- ord-7b3d35f9eec5401abafe481d8cf02aaf
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631379
Reaction notes
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