Trichlorophenoxyacetic acid → 3-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-benzoic acid methyl ester

HRID 1945376

Reaktionsgleichung

Reaktionsgleichung von HRID 1945376
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[C:10]([Cl:14])[C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])[CH:19]=1

Komponenten

6

Edukt 3

HCID 1480Trichlorophenoxyacetic acidHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 2724699PyBOP

Produkt 1

HCID 248110013-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-benzoic acid methyl esterAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The mixture of (2,4,5-trichloro-phenoxyacetic acid (127.8 mg, 0.5 mmol), 3-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol), 4-dimethylaminopyridine (122.2 mg, 1.0 mmol) and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (pybop) (520.3 g, 1.0 mmol) in DMF (5.0 mL) was stirred overnight and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 3-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (166.4 mg, 85.6% yield).

Aufarbeitung

  1. custompartitioned between ethyl acetate and 10% HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

Quellen und Nachweise

ORD-Eintrag
ord-abdd9bc9d0c347d5a931bf1da08883e2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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