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Thionyl Chloride → N-(4-Methoxybenzyl)-N-(6-(benzyloxy)naphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)-benzamide

HRID 1511450
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Reaktionsgleichung

Reaktionsgleichung von HRID 1511450
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1.[H-].[Na+].[CH3:26][O:27][C:28]1[CH:53]=[CH:52][C:31]([CH2:32][NH:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH:40]=3)[CH:35]=2)=[CH:30][CH:29]=1>C1COCC1>[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH2:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:40]=3)[CH:35]=2)[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:7]([O:6][CH3:5])=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH:9]=2)=[CH:52][CH:53]=1
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Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 25139545N-(4-Methoxybenzyl)-6-(benzyloxy)naphthalen-2-amineHCID 549124263',6-Dimethoxy-(1,1'-biphenyl)-3-carboxylic acid

Produkt 1

HCID 25140252N-(4-Methoxybenzyl)-N-(6-(benzyloxy)naphthalen-2-yl)-4-methoxy-3-(3-methoxyphenyl)-benzamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Thionyl chloride (308 μl, 502 mg, 4.22 mmol) was added to 4-methoxy-3-(3-methoxyphenyl)-benzoic acid (365 mg, 1.41 mmol) in anhydrous THF (4.75 mL) at room temperature, and the resulting solution was heated at reflux for 4.5 hours. The solvent was removed and the resulting acid chloride was used without further purification. Sodium hydride (85 mg, 2.12 mmol) was added to 37 (378 mg, 1.02 mmol) in anhydrous THF (7.50 mL). After stirring for two hours at room temperature, a solution of the freshly-prepared acid chloride (1.41 mmol) in anhydrous THF (2.40 mL) was added and the reaction was heated to reflux for 18 hours. The reaction was cooled, partitioned between saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (50 mL), then extracted with CH2Cl2 (3×100 mL). Combined organic extracts were washed with saturated aqueous NaCl solution (200 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 4:1:1 Hexanes:EtOAc:CH2Cl2) to give 38 as a brown-yellow amorphous solid (515 mg, 83%): 1H NMR (CDCl3, 500 MHz) δ 7.58 (d, J=9.0 Hz, 1H), 7.55 (d, J=8.7 Hz, 1H), 7.50-7.45 (m, 3H), 7.44-7.40 (m, 2H), 7.38-7.34 (m, 2H), 7.29 (d, J=2.2 Hz, 1H), 7.25 (m, 2H), 7.21 (dd, J=8.9, 2.6 Hz, 1H), 7.15 (d, J=2.4 Hz, 1H), 7.09 (m, 1H), 7.01 (dd, J=8.7, 2.1 Hz, 1H), 6.80 (m, 2H), 6.77 (ddd, J=8.2, 2.7, 0.9 Hz, 1H), 6.74 (d, J=8.7 Hz, 1H), 6.59-6.56 (m, 2H), 5.16 (s, 2H), 5.14 (s, 2H), 3.78 (s, 3H), 3.72 (s, 3H), 3.62 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 170.0, 159.3, 159.0, 157.6, 157.3, 139.9, 139.1, 136.8, 133.0, 132.4, 130.5, 130.1, 130.1 (2C), 129.6, 129.5, 129.1, 128.9, 128.9 (2C), 128.4, 128.2, 127.9, 127.7 (2C), 127.3, 125.8, 122.1, 120.0, 114.7, 114.0 (2C), 113.2, 110.4, 107.1, 70.3, 55.7, 55.4, 55.2, 53.9; IR (film) νmax 3059, 3032, 2999, 2934, 2835, 1636, 1601, 1506, 1456, 1389, 1248, 1209, 1026, 854, 818, 735, 698 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C40H35NO5, 610.2593; found, 610.2567.

Aufarbeitung

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 4.5 hours
  3. customThe solvent was removed
  4. customthe resulting acid chloride was used without further purification
  5. temperaturethe reaction was heated
  6. temperatureto reflux for 18 hours
  7. temperatureThe reaction was cooled
  8. custompartitioned between saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (50 mL)
  9. extractionextracted with CH2Cl2 (3×100 mL)
  10. washCombined organic extracts were washed with saturated aqueous NaCl solution (200 mL)
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was purified via column chromatography (SiO2, 4:1:1 Hexanes:EtOAc:CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f017110eb2a94466933c089c6f69f1d3
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08212012B2

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