Acetic Acid → 2-Amino-5-bromo-3-fluoro-N-methyl-benzamide

HRID 1041438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041438
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C(O)(=O)C.[Br:17]Br>>[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([Br:17])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 24408BromineHCID 272815042-Amino-3-fluoro-n-methylbenzamide

Produkt 1

HCID 672637462-Amino-5-bromo-3-fluoro-N-methyl-benzamide

Versuchsvorschrift

2-Amino-3-fluoro-N-methyl-benzamide (10.0 g, 59.5 mmol) was dissolved in acetic acid (100 mL, 176 mmol) and bromine (3.22 mL, 62.4 mmol) was added. The reaction was stirred at room temperature for 20 minutes and the precipitate was then collected by filtration and washed with ethyl ether. The white solid was dried overnight under high vacuum at 50° C. to obtain 2-amino-5-bromo-3-fluoro-N-methyl-benzamide; hydrobromide as a white solid (16.8 g, 86%). LCMS (m/e) 216 (M-NHCH3); 1H-NMR (d6-DMSO, 400 MHz) δ 8.49-8.38 (m, 1H), 7.83-7.46 (m, 3H), 7.54 (s, 1H), 7.43 (d, 1H, J=10.89 Hz), 2.72 (d, 3H, J=4.2 Hz); 19F-NMR (d6-DMSO, 400 MHz) δ 131.

Aufarbeitung

  1. filtrationthe precipitate was then collected by filtration
  2. washwashed with ethyl ether
  3. customThe white solid was dried overnight under high vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-17876468463145949e96dcec8c5f0a15
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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