Reaktionsgleichung
[CH3:1][N:2]([CH3:7])[S:3]([CH3:6])(=[O:5])=[O:4].C([Li])CCC.[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=O)[CH3:14].C[Si](C)(C)[N-:28][Si](C)(C)C.[Li+].B(F)(F)F.CCOCC>O1CCCC1>[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:19]([NH2:28])[CH2:6][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH3:14]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
1-(3-Ethoxy-4-methoxyphenyl)-2-(N,N-dimethylaminosulfonyl)ethylamine was prepared by a procedure analogous to that of Example 1 from N,N-dimethyl methanesulfonamide (685 mg, 5.56 mmol) and n-butyllithium (2.5 mL, 2.5 M, 6.3 mmol) in tetrahydrofuran (90 mL), and 3-ethoxy-4-methoxybenzaldehyde (1.0 g, 5.5 mmol), lithium hexamethyldisilazide (4.7 mL, 1.3 M, 6.1 mmol) and boron trifluoride etherate (1.4 mL, 11 mmol) in tetrahydrofuran (5 mL). The product was obtained as a white solid (360 mg, 21% yield): mp, 82.0-83.0° C.; 1H NMR (CDCl3); δ 1.48 (t, J=7.5 Hz, 3H, CH3), 1.91 (br s, 2H, NH2), 2.88 (s, 6H, N(CH3)2), 3.05 (dd, J=3.0, 13.5 Hz, 1H, CHH), 3.12 (dd, J=9.2, 13.5 Hz, 1H, CHH), 3.88 (s, 3H, CH3), 4.12 (q, J=7.0 Hz, 2H, CH2), 4.61 (dd, J=2.9, 9.2 Hz, 1H, NCH), 6.83-6.99 (m, 3H, Ar); 13C NMR (CDCl3) δ 14.81; 37.42, 51.02, 56.03, 64.41, 110.74, 111.55, 118.35, 135.97, 148.64, 148.96; Anal Calcd for C13H22NO4S: C, 51.64; H, 7.33; N, 9.26. Found: C, 51, 41; H, 7.11; N, 9.10.
Quellen und Nachweise
- ORD-Eintrag
- ord-a585eb53beb84bba9f645a6176057f30
- Quelldatensatz
- uspto-grants-2000_02
- Patentnummer
- US06020358
Verknüpfte Notizen
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