Triethylamine → HCID 86707234, compound
Reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH:4]=[CH:5][C:6](=[CH:11][N:12]1CCCC1)[CH:7]([S:9][CH3:10])[CH3:8].C(N(CC)CC)C.Cl.N[OH:29]>C1(C)C=CC=CC=1>[CH3:10][S:9][CH:7]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:18])[F:1])=[N+:12]([O-:29])[CH:11]=1)[CH3:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 12.800000190734863 °C
Procedure
403 mg (0.37 mmol) of the 27 wt % 1,1,1-trifluoro-6-(methylthio)-5-(pyrrolidine-1-ylmethylene)hept-3-en-2-one (4) in toluene was added to a 25 mL three-neck round bottom flask equipped with a reflux condenser and vented to a bleach scrubber. To this mixture was added 34 mg (0.34 mmol) of triethylamine in one portion. The reaction mixture was cooled to about 12.8° C. and then 24 mg (0.34 mmol) of hydroxylamine hydrochloride was added in one portion. The reaction mixture was slowly heated to 85° C. and stirred for one hour and forty-five minutes. The reaction mixture was then cooled to ambient temperature. This mixture was split into many fractions for instrumental analysis and purification. A portion of the reaction mixture was partitioned between toluene and water. Both the organic and aqueous layers were analyzed by LC/MS. Both layers were confirmed to have a peak with molecular consistency for 5-(1-(methylthio)ethyl)-2-(trifluoromethyl)pyridine N-oxide (C9H10F3NOS). Calculated m/z=237.04. Found m/z=237.04.
Workup
- customequipped with a reflux condenser
- temperatureThe reaction mixture was slowly heated to 85° C.
- temperatureThe reaction mixture was then cooled to ambient temperature
- customThis mixture was split into many fractions for instrumental analysis and purification
- customA portion of the reaction mixture was partitioned between toluene and water
Sources & evidence
- ORD record
- ord-1bd6777ac0db4e77874c4096d47050ec
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785480B2
Reaction notes
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