Triethylamine → 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide

HRID 238881

Reaktionsgleichung

Reaktionsgleichung von HRID 238881
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.[CH3:31][NH:32][O:33][CH3:34]>C(Cl)Cl>[F:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([N:32]([O:33][CH3:34])[CH3:31])=[O:7])=[CH:3][C:2]=1[OH:1]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5936354-Fluoro-3-hydroxybenzoic acid

Produkt 1

HCID 594590524-fluoro-3-hydroxy-N-methoxy-N-methylbenzamideAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

To a 5 L four necked round bottom flask was added 3-hydroxy-4-fluorobenzoic acid (100 g, 0.64 mol) and CH2Cl2 (2.3 L). Triethylamine (107 mL, 0.768 mol) was then added to the suspension. The solution was cooled to 78° C., and EDCI (184.2 g, 0.961 mol) was added portion wise followed by the addition of N,O-dimethylhydroxyamine hydrochloride (93.6 g, 0.96 mol). The reaction mixture was stirred at −78° C. for 1 h and then allowed to warm to 0° C. over a period of 2 h. The reaction mixture was transferred to a separatory funnel and washed water (2×1.2 L). The organic portion was dried over Na2SO4, filtered and concentrated in vacuo to give 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide as a white solid (94.4 g, 74%).

Aufarbeitung

  1. temperatureto warm to 0° C. over a period of 2 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. washwashed water (2×1.2 L)
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d9df3936e90440e83792b9d6c12401f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642576B2

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