1,2-Dichloroethane → 2-Amino-5-fluoro-N-methoxy-N-methylbenzamide

HRID 19675

Reaktionsgleichung

Reaktionsgleichung von HRID 19675
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][O:12][NH:13][CH3:14].[NH2:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18](O)=[O:19].C(Cl)CCl>C(Cl)(Cl)Cl.C(Cl)Cl>[NH2:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([N:13]([O:12][CH3:11])[CH3:14])=[O:19]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 1014122-Amino-5-fluorobenzoic acid

Produkt 1

HCID 534075722-Amino-5-fluoro-N-methoxy-N-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. mixture of diisopropylethylamine (34.36 mL, 197.25 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (19.24 g, 197.25 mmol) in CHCl3 (300 mL) was added 2-amino-5-fluorobenzoic acid (25.50 g, 164.38 mmol) followed by EDC (31.51 g, 164.38 mmol). The reaction was stirred from 0° C. to ambient temperature over 2 h and then diluted with CH2Cl2 (100 mL), washed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase chromatography (3-8% MeOH/CH2Cl2) yielded 2-amino-5-fluoro-N-methoxy-N-methylbenzamide as a yellow oil. 1H NMR (CDCl3, 400 MHz) 7.12 (m, 1H, ArH); 6.93 (m, 1H, ArH); 6.65 (m, 1H, ArH); 3.63 (s, 3H, CH3); 3.35 (s, 3H, CH3); MS (Electrospray): m/z 199.1 (M+H).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by normal phase chromatography (3-8% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3d66f49508da4beb9babdb20a9d84317
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745452B2

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