Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide

HRID 83857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83857
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][C:3]=1[O:14][CH3:15].Cl.[CH3:17][NH:18][O:19][CH3:20].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([N:18]([O:19][CH3:20])[CH3:17])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15]

Komponenten

6

Edukt 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667403622-(4-Chloro-3-methoxyphenyl)-2-methylpropanoic acid

Produkt 1

HCID 866622432-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-chloro-3-methoxyphenyl)-2-methylpropanoic acid (15) (268 g, 1.17 mol) in CH2Cl2 (1.7 L) was added N,O-dimethylhydroxylamine hydrochloride (137 g, 1.4 mol), EDCl (270 g, 1.4 mol), and DMAP (172 g, 1.4 mol ). The resulting mixture was stirred for 3 h and washed with 10% citric acid solution (1.5 L), satd NaHCO3 (1.5 L), and brine(1.5 L) successfully. The organic phase was dried over MgSO4, filtered, and concentrated at reduced pressure to afford 2-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide (16) as a brown solid (276 g, 96%). 1H NMR (400 MHz, CDCl3): δ 7.30-7.32 (d, 1H), 6.81-6.84 (m, 3H), 3.89 (s, 3H), 3.12 (s, 3H), 2.78 (s, 3H), 1.53 (s, 6H).

Aufarbeitung

  1. washwashed with 10% citric acid solution (1.5 L), satd NaHCO3 (1.5 L), and brine(1.5 L) successfully
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-255fce8739a14fbfa8332581e445d771
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846739B2

Notizen zur Reaktion

Wird geladen…