Reaktion #1383378

ord-5a1341bed4614c468d89a9aaf9bf12f3

Reaktionsgleichung

NC(CO)CO
2-Amino-1,3-dihydroxypropane
C[O-].[Na+]
sodium methylate
COC(=O)c1cc(N)cc(C(=O)OC)c1
5-amino-1,3-benzenedicarboxylic acid dimethyl ester
Nc1cc(C(=O)NC(CO)CO)cc(C(=O)NC(CO)CO)c1
5-amino-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide
Ausbeute 93.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture is heated to the reflux temperature
  2. 2
    Sonstigeto get a solution
  3. 3
    Filtrationis filtered
  4. 4
    Filtrationthe solid on filter
  5. 5
    Waschenis washed with methanol (40 mL)
  6. 6
    Sonstigedried
  7. 7
    Sonstigeyielding the product of the title (43.5 g, 133 mmol, yield: 93%)

Vorschrift

2-Amino-1,3-dihydroxypropane (27.4 g, 300 mmol) and 1.5M solution of sodium methylate in methanol (14.3 mL, 21.5 mmol) are added to a suspension of 5-amino-1,3-benzenedicarboxylic acid dimethyl ester (30.0 g, 143 mmol) in methanol (0.2 L). The reaction mixture is heated to the reflux temperature to get a solution. After 2.5 hours of reflux and 4 hours at room temperature the reaction mixture is filtered and the solid on filter is washed with methanol (40 mL) and dried yielding the product of the title (43.5 g, 133 mmol, yield: 93%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07244864B2uspto-grants-2007_07