1,1'-Carbonyldiimidazole → 2-amino-N,6-dimethoxybenzamide

HRID 1045972

Reaktionsgleichung

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=O.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1.C([N:28](C(C)C)CC)(C)C>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH:28][O:19][CH3:18])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 21 °C

Versuchsvorschrift

A mixture of 2-amino-6-methoxybenzoic acid (4.6 g, 27.52 mmol) and carbonyl-1,1′-dimidazole (5.35 g, 33.02 mmol) in THF (70 ml) was stirred at 21° C. under nitrogen for 3 days. N,N-diisopropyl-N-ethyl-amine (1.667 ml, 9.57 mmol) and O-methylhydroxylaminehydrochloride (0.545 ml, 7.18 mmol) were added. The solution was heated to 50° C. for 3 hours. After cooling and concentration under vacuum, the reaction mixture was diluted with EtOAc, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, dried over magnesium sulfate, concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM to afford 2-amino-N,6-dimethoxybenzamide (318 mg, 33.9%) as a white solid. Mass spectrum: MH+ 197; NMR Spectrum: (DMSOd6) 3.67 (s, 3H), 3.71 (s, 3H), 5.57 (bs, 2H), 6.19 (d, 1H), 6.31 (d, 1H), 7.02 (dd, 1H)

Aufarbeitung

temperatureThe solution was heated to 50° C. for 3 hours
temperatureAfter cooling
concentrationconcentration under vacuum
additionthe reaction mixture was diluted with EtOAc
washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag: ord-4eeda08fd5ba448a9af5234e19039102
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08569298B2

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