Sodium Hydroxide → 3-Ureidomethyl-phthalic acid

HRID 448433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448433
[OH-].[Na+].C[O:4][C:5](=[O:21])[C:6]1[C:7](=[C:12]([CH2:16][NH:17][C:18]([NH2:20])=[O:19])[CH:13]=[CH:14][CH:15]=1)[C:8]([O:10]C)=[O:9]>O.C(O)C>[NH:17]([CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:6]([C:5]([OH:21])=[O:4])[C:7]=1[C:8]([OH:10])=[O:9])[C:18]([NH2:20])=[O:19]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 672293263-Ureidomethyl-phthalic acid dimethyl ester

Produkt 1

HCID 672298293-Ureidomethyl-phthalic acidAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium hydroxide (0.4 g, 10.5 mmol) in water (10 mL) was added to a stirred suspension of 3-ureidomethyl-phthalic acid dimethyl ester (1.4 g, 5.3 mmol) in ethanol (30 mL). The mixture was refluxed for one hour and then cooled to room temperature. The mixture was concentrated, and the residue was dissolved in water (30 mL). The mixture was acidified with 4N HCl to pH 1. The mixture was filtered to give 3-ureidomethyl-phthalic acid (1.0 g, 76%): 1H NMR (DMSO-d6) δ 4.22 (d, J=5.9 Hz, 2H, CH2), 5.68 (s, 2H, NH2), 6.40 (t, J=6.0 Hz, 1H, NH), 7.46-7.56 (m, 2H, Ar), 7.73 (d, J=6.9 Hz, 1H, Ar), 13.23 (b, 2H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for one hour
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in water (30 mL)
  4. filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-9393a3bc94ee44bfb39e9699d66ec78e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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