N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide → N,N-dimethyl 4-amino-3-methylphenoxyacetamide

HRID 1584133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584133
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(OC(C)(C)C)=O)=[C:8]([CH3:20])[CH:7]=1>FC(F)(F)C(O)=O>[CH3:22][N:2]([CH3:1])[C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:20])[CH:7]=1

Komponenten

3

Edukt 1

HCID 15870806N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide

Produkt 1

HCID 15870807N,N-dimethyl 4-amino-3-methylphenoxyacetamideAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a 200 mL round bottomed flask with a stirring bar and a drying tube was added N,N-dimethyl 4-(1,1-dimethylethoxycarbonyl)amino-3-methyphenoxyacetamide (1.00 g, 3.24 mmol) and trifluoroacetic acid (20 mL). This solution was stirred at ambient temperature 48 h. The trifluoroacetic acid was removed in vacuo and the residue was dissolved in 200 mL of EtOAc. This solution was washed with NaHCO3 solution and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave 0.493 g (73% yield) of N,N-dimethyl 4-amino-3-methylphenoxyacetamide as white crystals. 1H NMR (CDCl3): d 2.15 (s, 3H), 2.97 (s, 3H), 3.08 (s, 3H), 3.27 (br s, 2H), 4.59 (s, 2H), 6.71 (m, 3H). ##STR52## N,N-Dimethyl-2-(4-amino-3-methylphenoxy)ethylamine (5-4)

Aufarbeitung

  1. customThe trifluoroacetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in 200 mL of EtOAc
  3. washThis solution was washed with NaHCO3 solution and brine
  4. customDrying
  5. filtration(MgSO4), filtration and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-65de6b4fee5e49bc8336a46039e5ca1e
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932582

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