Benzene → 4-Ethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid, (2,2,3,3,3-pentafluoropropylidene] hydrazide
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=[C:6]([C:21]([NH:23][NH2:24])=[O:22])[CH:5]=1)[CH3:2].O.[F:26][C:27]([F:34])([C:30]([F:33])([F:32])[F:31])[CH:28]=O.C1C=CC=CC=1.Cl>C(OCC)(=O)C.O>[F:26][C:27]([F:34])([C:30]([F:33])([F:32])[F:31])[CH:28]=[N:24][NH:23][C:21](=[O:22])[C:6]1[CH:5]=[C:4]([NH:3][CH2:1][CH3:2])[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)[N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
4-ethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide (0.30 g, 0.00088 mol) was mixed with 2,2,3,3,3-pentafluoropropionaldehyde monohydrate (0.29 g, 0.00088×2.0 mol) and benzene, and further with a small amount of concentrated hydrochloric acid. The obtained mixture was refluxed and dehydrated for about 8 hours using a water separator. The obtained reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and the organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated. The obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.
Workup
- temperatureThe obtained mixture was refluxed
- customThe obtained reaction solution
- customthe organic phase separated from the solution
- washwas washed with saturated brine
- dry with materialdried with anhydrous sodium sulfate
- concentrationconcentrated
- customThe obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-d3f072e4dd1d40f7b6aa90062e8d9b35
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159901
Reaction notes
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