Dimethyl 5-aminoisophthalate → 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide

HRID 1296196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296196
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[CH3:7][O-:8].[Na+].CO[C:12]([C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[C:16]([C:21]([O:23]C)=O)[CH:15]=1)=[O:13]>CO>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:1][CH:2]([CH2:3][OH:4])[CH2:7][OH:8])=[O:13])[CH:15]=[C:16]([C:21]([NH:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4])=[O:23])[CH:17]=1

Komponenten

5

Edukt 3

HCID 66831Dimethyl 5-aminoisophthalateHCID 68294SerinolHCID 10942334Sodium Methoxide

Produkt 1

HCID 99452455-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  1. temperatureThe reaction mixture is heated to the reflux temperature
  2. customto get a solution
  3. filtrationis filtered
  4. filtrationthe solid on filter
  5. washis washed with methanol (40 mL)
  6. customdried
  7. customyielding the product of the title (43.5 g, 133 mmol, yield: 93%)

Quellen und Nachweise

ORD-Eintrag
ord-5a1341bed4614c468d89a9aaf9bf12f3
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244864B2

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