Triethylamine → N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2-naphthylethanamide

HRID 431395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 431395
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C=1.[C:23]1(CC(Cl)=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[CH3:44][C:45](N(C)C)=[O:46]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:45](=[O:46])[CH2:44][C:25]2[CH:24]=[CH:23][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:5][C:4]=1[O:10][CH2:11][C:12]1[C:19]2[C:20](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:21]=[CH:22][CH:13]=1

Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 27953862-(Naphthalen-1-yl)acetyl chlorideHCID 699120564-Methoxy-3-(2-naphthylethoxy)phenylamine

Produkt 1

HCID 69912076N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2-naphthylethanamide

Versuchsvorschrift

N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2-naphthylethanamide (Exemplary Compound 48) was prepared using the same experimental conditions used to prepare Exemplary Compound 52 (Scheme X, above). From 4-methoxy-3-(2-naphthylethoxy)phenylamine (350 mg, 1.25 mmol) and 1-naphthylacetyl chloride (260 mg, 1.25 mmol) in 10 mL of dimethyl acetamide containing triethylamine (1 mL, 7.17 mmol) stirred at room temperature for 16 h., was obtained 370 mg of product in (66%) yield as off white needles after recrystallization from ethyl acetate/hexane: mp 161-163° C. 1H NMR (400 MHz, Me2SO-d6) δ3.69 (s, 3H); 4.11 (s, 2H); 5.45 (s, 2H); 6.93 (d, 1H, J=8.8); 7.18 (dd, 1H, J=2.3, 8.7); 7.46-7.64 (m, 9H); 7.82-8.15 (m, 6H); 10.20 (s, 1H). Anal. Calcd for C30H25NO3: C, 80.51; H, 5.63; N, 3.13. Found: C, 80.38; H, 5.70; N, 3.12.

Quellen und Nachweise

ORD-Eintrag
ord-08650cdeb37a45eda2dc4d71b6e05d67
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06656971B2

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