p-Toluenesulfonic acid → HCID 86616712, compound
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[C:5]([C:19]#[N:20])=[C:4]([C:21]#[N:22])[C:3]=1[S:23]([C:25]([F:28])([F:27])[F:26])=[O:24].[CH:29](OCC)(OCC)[O:30][CH2:31][CH3:32].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=[C:8]([Cl:18])[C:7]=1[N:6]1[C:2]([N:1]=[CH:29][O:30][CH2:31][CH3:32])=[C:3]([S:23]([C:25]([F:27])([F:26])[F:28])=[O:24])[C:4]([C:21]#[N:22])=[C:5]1[C:19]#[N:20]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-2,3-dicyano-4-trifluoromethylsulfinylpyrrole (290 mg, 0.6 mmol), triethyl orthoformate (4.45 g, 29.7 mmol), and p-toluenesulfonic acid (10 mg, 0.1 mmol) was heated at 100° C. for 40 minutes, then at 120° C. for 70 minutes. Additional p-toluenesulfonic acid (a catalytic amount) was added and the resulting mixture was heated at 120° C. for 2.4 hour. It was then concentrated to dryness and diluted with dichloromethane (20 ml). The organic layer was washed with saturated sodium bicarbonate, brine, dried (sodium sulfate), and concentrated to afford the title compound as an orange oil which was used without purification for the next transformation. 19F-NMR: −64.23, −72.08.
Workup
- temperaturethe resulting mixture was heated at 120° C. for 2.4 hour
- concentrationIt was then concentrated to dryness
- additiondiluted with dichloromethane (20 ml)
- washThe organic layer was washed with saturated sodium bicarbonate, brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5927f07bece74c9d9198136a389638f7
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674474B2
Reaction notes
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