Acetyl chloride → n-(3,4-Dichlorobenzyl)-n-methyl-acetamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][NH:6][CH3:7].[C:12](Cl)(=[O:14])[CH3:13]>O1CCCC1.C([O-])(=O)C.[Na+].C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][N:6]([CH3:7])[C:12](=[O:14])[CH3:13]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A solution of (3,4-dichlorobenzyl)-methylamine (0.50 g, 2.63 mmol) (Shapiro et al. J. Amer. Chem. Soc., (1959) 81, 3725) in a mixture of tetrahydrofuran (20 ml) and 40% aqueous sodium acetate (10 ml) was cooled to 0–5° C. (ice bath) and treated with a solution of acetyl chloride (0.3 g in tetrahydrofuran) added dropwise over 5 min. After 1 h at 0–5° C., the reaction mixture was diluted with ethyl acetate, washed successively with 1 N hydrochloric acid, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and distillation of the residue in vacuo gave 0.51 g (83% yield) of the title amide as a clear oil: bp 110–120° C./0.2 torr, (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm), mixture of rotamers: 2.36 and 2.39 (3H, 2 s, COCH3), 3.16 (3H, s, NCH3), 4.70 and 4.75 (2H, 2 s, NCH2), 7.2–7.7 (3H, m, aromatics). Anal. calcd for C10H11Cl2NO: C, 51.74; H, 4.78; N, 6.03. Found: C, 51.70; H, 4.77; N, 6.04.
Aufarbeitung
- temperaturewas cooled to 0–5° C. (ice bath)
- additionadded dropwise over 5 min
- washwashed successively with 1 N hydrochloric acid, saturated sodium bicarbonate, brine
- dry with materialdried (magnesium sulfate)
- customEvaporation of the solvent and distillation of the residue in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-ac152c43908d4ff39855d100fb06d176
- Quelldatensatz
- uspto-grants-2006_09
- Patentnummer
- US07109186B2
Notizen zur Reaktion
Wird geladen…