Triethylamine → N-(3,5-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

HRID 2214708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214708
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.Cl.[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:18][NH:19][CH3:20].CCN(CC)CC>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:18][N:19]([CH3:20])[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 174805Benzenemethanamine, 3,5-dichloro-N-methyl-, hydrochlorideHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Produkt 1

HCID 69655600N-(3,5-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (0.96 g, 5 mmol) in CH2Cl2 (20 mL) was added a solution of 3,5-dichlorobenzyl-methylamine hydrochloride (1.133 g, 5 mmol) and Et3N (2 mL) in CH2Cl2 (25 mL). The addition flask was rinsed with CH2Cl2 (5 mL) and added to the reaction mixture. After 2 h, the reaction mixture was concentrated and the resulting residue was triturated with ether (100 mL), filtered and concentrated to give the desired product as a viscous brown oil (1.70 g, 100% yield). 1HNMR (300 MHz, CDCl3) δ: 7.30–7.27 (1H, m), 7.16 (1.5H, br s), 7.06 (0.5H, s), 6.17 (0.66H, s), 6.07 (0.34H, s), 4.59 (1.33H, s), 4.53 (0.67H, s), 3.03 (2H, s), 2.97 (1H, s), 1.74 (4H, s), 1.70 (2H,s).

Aufarbeitung

  1. washThe addition flask was rinsed with CH2Cl2 (5 mL)
  2. additionadded to the reaction mixture
  3. concentrationthe reaction mixture was concentrated
  4. customthe resulting residue was triturated with ether (100 mL)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4a8138d189534cfabd82e09fba9f1f88
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109186B2

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