1,2-Dichloroethane → 3-[2-(2,4,5-Trichloro-phenoxy)acetyl-amino]-benzamide

HRID 1945385

Reaktionsgleichung

Reaktionsgleichung von HRID 1945385
[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.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[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]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20])=[O:8]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 1480Trichlorophenoxyacetic acidHCID 16453-AminobenzamideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Produkt 1

HCID 248111053-[2-(2,4,5-Trichloro-phenoxy)acetyl-amino]-benzamideAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the 2,4,5-trichloro-phenoxy acetic acid (76.7 mg, 0.3 mmol), 3-amino benzamide (61.3 mg, 0.45 mmol), EDC (86.3 mg, 0.45 mmol) and HOBt (61.3 mg, 0.45 mmol) were dissolved in DMF (3 mL), and DIPEA (0.08 mL, 0.45 mmol) were added. The reaction mixture was stirred at room temperature overnight, and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (CH2Cl2:MeOH=6:3:1) gave 3-[2-(2,4,5-trichloro-phenoxy)acetyl-amino]-benzamide as a white solid (95.2 mg, 84.9% yield).

Aufarbeitung

  1. custompartitioned between Ethyl acetate and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (CH2Cl2:MeOH=6:3:1)

Quellen und Nachweise

ORD-Eintrag
ord-1638c6b9dae34265b2de453734b00d69
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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