Water → 1-Methyl-4-(trifluoromethyl)pyrrole-3-carbonitrile
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([C:11](O)=O)=[CH:3]1.ClS([N:18]=C=O)(=O)=O.CN(C)C=O.O>C(#N)C.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([C:11]#[N:18])=[CH:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylic acid (1.93 g, 0.01 mol) in acetonitrile at 40°-45° C. is treated dropwise with chlorosulfonylisocyanate (1.41 g, 0.01 mol), heated at 40° C. for 24 hours, cooled to room temperature, treated with dimethylformamide (1.46 g, 0.02 mol), heated at 40° C. for 8 hours, cooled to room temperature, stirred for 48 hours at room temperature and poured into water. The resultant mixture is extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, dried (MgSO4) and concentrated in vacuo to afford an oily solid residue. The residue is taken up ethyl acetate, washed with 1% aqueous sodium hydroxide, dried (MgSO4) and concentrated in vacuo to give a yellow oil residue. Kugelrohr distilllation at 100°-110° C./2 mm Hg yields the title product as a white solid, 0.95 g (54%).
Workup
- temperaturecooled to room temperature
- temperatureheated at 40° C. for 8 hours
- temperaturecooled to room temperature
- extractionThe resultant mixture is extracted with ethyl acetate
- washwashed sequentially with water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto afford an oily solid residue
- washwashed with 1% aqueous sodium hydroxide
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give a yellow oil residue
Sources & evidence
- ORD record
- ord-315281094e7643d5919ed6489f56abb7
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05204332
Reaction notes
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