Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86672057, Verbindung

HRID 1261778

Reaktionsgleichung

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:20]([O:21][CH3:22])[CH3:19])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A solution of 4-chloro-2-phenylamino-benzoic acid (10.1 g, 41.0 mmol) in N,N-dimethylformamide (200 mL) at 25° C. was treated with O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (31.2 g, 82.0 mmol), N,O-dimethyl hydroxylamine hydrochloride (7.94 g, 82.0 mmol), and N,N-diisopropylethylamine (45.0 g, 350 mmol). The resulting mixture was stirred at 25° C. for 24 h. At this time, the reaction mixture was diluted with ethyl acetate (600 mL) and washed with water (4×200 mL) and a saturated aqueous sodium chloride solution (1×200 mL). The organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (silica gel, 100-200 mesh, ethyl acetate/hexanes 10-25%) afforded 4-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide (6.62 g, 56.4%) as a yellow solid. 1H NMR (DMSO-d6) δ ppm 7.93 (s, 1H), 7.20-7.39 (m, 3H), 7.02-7.17 (m, 3H), 6.88-6.99 (m, 2H), 3.50 (s, 3H), 3.20 (s, 3H); MS m/e calcd for C15H15ClN2O2 [(M+H)+] 291.0. Found 291.0; [(M−C2H6NO)+] 230.0. Found 230.0.

Aufarbeitung

washwashed with water (4×200 mL)
dry with materialThe organics were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-66d8c2f510d647ff849910715cc8485d
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08471027B2

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