Triethylamine → 4-Dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide

HRID 1274823Notes

Reaction equation

HRID 1274823 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([OH:22])=O)[CH:4]=1.S(Cl)(Cl)=O.C([N:35](CC1C=CC=CC=1)[NH2:36])C1C=CC=CC=1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O.C1C=CC=CC=1>[CH3:23][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=2)[N:6]=[C:5]([C:20]([NH:35][NH2:36])=[O:22])[CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1970501,1-DibenzylhydrazineHCID 21249828HCID 21249828, compound

Product 1

HCID 702694074-Dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid (0.64 g, 0.0020 mol) was mixed with thionyl chloride (0.50 g, 0.0020×2.1 mol) and benzene (about 10 ml), and further with a small amount of dimethyl formamide. Thereafter, the resultant mixture was refluxed for about 30 minutes. The obtained reaction solution was concentrated and then dissolved in dichloromethane (about 30 ml). The obtained solution was mixed with N,N-dibenzyl hydrazine (0.66 g, 0.0020×1.6 mol) and further with triethyl amine (0.53 g, 0.0020×2.6 mol). After the resultant mixture was stirred at room temperature for about one hour, 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

  1. customThe obtained reaction solution
  2. concentrationwas concentrated
  3. dissolutiondissolved in dichloromethane (about 30 ml)
  4. customthe obtained reaction solution
  5. customthe organic phase separated from the solution
  6. washwas washed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87882489d3eb4683891ddb592a914c36
Source dataset
uspto-grants-2000_12
Patent number
US06159901

Reaction notes

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