Methylamine → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

HRID 924697

Reaktionsgleichung

Reaktionsgleichung von HRID 924697
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.CN.Cl.[CH3:23][N:24](C)CCCC(N=C=N)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10]([NH:24][CH3:23])=[O:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 576913963-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

Produkt 1

HCID 593319703-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-prop ionic acid (0.25 g, 0.74 mmol) and 1-hydroxybenatriazole (0.12 g, 0.88 mmol) in dichloromethane (3 ml) was stirred for 15 minutes before addition of methylamine (40% solution in water, 0.11 μl, 1.47 mmol) and 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.17 g, 0.88 mmol). The reaction mixture was stirred for 16 hours, solvent removed under reduced pressure and the residue partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated sodium hydrogen carbonate, brine, dried (MgSO4), filtered and concentrated to yield the title compound which was used in the next step without further purification. LC/MS: (PS-A2) Rt 3.20 [M+H]+ 353.95.

Aufarbeitung

  1. customsolvent removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-29d9a9eb645b42089d18a71c71f5b83c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283226B2

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