Triethylamine → HCID 15906613, compound

HRID 1250504Notes

Reaction equation

HRID 1250504 reaction equation
[CH3:1][O:2][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.Cl.[O:28]([NH2:30])[CH3:29].C(N(CC)CC)C>C(OCC)(=O)C.CN(C=O)C.C1C=CC=CC=1>[CH3:29][O:28][NH:30][C:20]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[N:6]=1)=[O:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 109030764-Methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid

Product 1

HCID 15906613HCID 15906613, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.4 g (0.00128 mol) of 4-methoxy-6-{3-(trifluoromethyl)phenoxy)-2-pyridine carboxylic acid was mixed with 0.3 g (0.00128×2.0 mol) of thionyl chloride and then with about 10 ml of benzene and a small amount of DMF, followed by treating the obtained mixture under reflux for about 30 minutes. The reaction solution was concentrated and mixed with methylene chloride and then with 0.21 g (0.00128×2.0 mol) of methoxylamine hydrochloride and 0.33 g (0.00128×2.5 mol) of triethyl amine, followed by stirring at room temperature for about one hour. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. additionby treating the obtained mixture
  2. temperatureunder reflux for about 30 minutes
  3. concentrationThe reaction solution was concentrated
  4. additionmixed with methylene chloride
  5. washwashed with saturated brine
  6. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-68cb5e2d217c44cdbf0fb9dece2826b1
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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