Triethylamine → 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 448931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448931
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:44]([C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[NH:48][CH3:49])[CH3:45]>O.ClCCl>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([N:48]([C:47]1[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=1[O:44][CH3:45])[CH3:49])=[O:9]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110213535-Bromo-4-chloro-2-hydroxybenzoic acid

Produkt 1

HCID 686025845-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamideAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4-chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR=2.60 min (method 1)

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel flash column chromatography
  7. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ef986d9651474386bb399580f066a497
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481738B2

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