1,2-Dichloroethane → 2-(Benzyl-methyl-amino)-N-methoxy-N-methy-acetamide

HRID 480243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480243
Cl.[CH2:2]([N:9]([CH2:11][C:12]([OH:14])=O)[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)CCl.Cl.[CH3:20][NH:21][O:22][CH3:23].CN1CCOCC1>CN(C=O)C>[CH2:2]([N:9]([CH3:10])[CH2:11][C:12]([N:21]([O:22][CH3:23])[CH3:20])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 457924962-(Benzyl(methyl)amino)acetic acid hydrochloride

Produkt 1

HCID 187689882-(Benzyl-methyl-amino)-N-methoxy-N-methy-acetamideAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(Benzyl-methyl-amino)-acetic acid hydrochloride salt (12 g, 56 mmol, 1.0 equiv) was mixed in DMF (200 mL) along with EDC (10.6 g, 56 mmol, 1.0 equiv) for 15 min. N,O-Dimethylhydroxylamine hydrochloride (6.52 g, 67 mmol, 1.2 equiv) was added to the reaction followed by N-methylmorpholine (34 mL, 334 mmol, 6.0 equiv). The reaction was stirred for 16 h. The DMF was removed in vacuo and the residue was redissolved in 200 mL of EtOAc. The solution was washed once with 200 mL brine. The organic layer was dried over Na2SO4, decanted and concentrated to yield the desired product as a free-flowing oil (12.6 g, 80%) that was used in the next step without further purification; MS, m/z 223=M+1.

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was redissolved in 200 mL of EtOAc
  3. washThe solution was washed once with 200 mL brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8410779ee1ba479086877a6f0b6e9fb8
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649642B2

Notizen zur Reaktion

Wird geladen…