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Benzoyl chloride → [4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 1468461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468461
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 86694946[4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Produkt 1

HCID 86695035[4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl esterAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of [4-(4-amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (115 mg, 0.34 mmol) and benzoyl chloride (52.64 mg, 0.37 mmol) were mixed together in dichloromethane (5 mL) under nitrogen and then diisopropylethylamine (0.12 mL, 0.67 mmol) was added to afford clear solution. The resulting solution was stirred for 4 hours at room temperature and then concentrated. Ethyl acetate (20 mL) was added and the mixture was washed with water (20 mL) and brine solution (20 mL) and then dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave a crude residue which was purified using an ISCO (12 g) column, eluting with 5-35% ethyl acetate in hexanes, to afford [4-(4-benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (133 mg, 88.8%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.46 (s, 1 H), 7.93-8.03 (m, 5 H), 7.88 (s, 1 H), 7.51-7.68 (m, 3 H), 7.48 (dd, J=8.6, 1.8 Hz, 1 H), 7.23 (d, J=8.5 Hz, 2 H), 7.18 (d, J=1.8 Hz, 1 H), 3.97 (s, 2 H), 3.66 (s, 3 H), 2.10 (s, 3 H). HRMS calcd. for C27H23ClNO3 [(M+H)+] 444.1361, obsd. 444.1361.

Aufarbeitung

  1. customto afford clear solution
  2. concentrationconcentrated
  3. additionEthyl acetate (20 mL) was added
  4. washthe mixture was washed with water (20 mL) and brine solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and concentration of the solvent under vacuum
  7. customgave a crude residue which
  8. customwas purified
  9. washeluting with 5-35% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a0dcc612756843588b0446afd70f304d
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000044B2

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