Triethylamine → Methyl 4-(2-chloro-5-fluoro-benzoylamino)-3-methoxybenzoate

HRID 2246066

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:11][CH3:12])[CH:5]=1.CCN(CC)CC.[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:23]=1[C:24](Cl)=[O:25]>ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:24](=[O:25])[C:23]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:22]=2[Cl:21])=[C:6]([O:11][CH3:12])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A dry, 3-L, 3-necked, round-bottomed flask equipped with a thermometer and addition funnel was charged a solution of 33 (96 g, 0.53 mol, 1.0 equiv.) and Et3N (88 ml, 0.64 mol, 1.2 equiv.) in dichloromethane (1.2 L). The solution was cooled to 0° C. by an ice bath and 2-chloro-5-fluoro-benzoyl chloride (110 g, 0.57 mol, 1.05 equiv.) was added drop-wise over 40 min at 0° C. After the addition, the reaction mixture was stirred at 0° C. for further 1.5 h. The organic layer was washed with brine three times, dried over MgSO4, filtered, and evaporated to yield 4-(2-chloro-5-fluoro-benzoylamino)-3-methoxy-benzoic acid methyl ester 34 as a white solid. 1H NMR (400 MHz, CDCl3) δ: 8.84 (s, 1H), 8.61 (d, 1H), 7.75 (dd, 1H), 7.60 (d, 1H), 7.55 (dd, 1H), 7.45 (dd, 1H), 7.20-7.13 (m, 1H), 3.97 (s, 3H), 3.93 (s, 3H). MS (ES) m/z 338.0 (MH)+.

Aufarbeitung

additionAfter the addition
washThe organic layer was washed with brine three times
dry with materialdried over MgSO4
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-cffc43d0eb6a4e21a772e87038afae48
Quelldatensatz: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07687494B2

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