Hydrochloric Acid → (2,4-Dimethoxy-benzylamino)-acetic acid

HRID 67405

Reaktionsgleichung

Reaktionsgleichung von HRID 67405
NCC(O)=O.COC1C=C(OC)C=CC=1C=O.[OH-].[Na+].Cl.[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][NH:26][CH2:27][C:28]([OH:30])=[O:29].[Cl-].[Na+].[C:39]12[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=1)[NH:44][C:43](=[O:50])[O:42][C:40]2=O>CO.CS(C)=O.[Pd].O>[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][NH:26][CH2:27][C:28]([OH:30])=[O:29].[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][N:26]1[C:40](=[O:42])[C:39]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[NH:44][C:43](=[O:50])[CH2:27]1

Komponenten

13

Edukt 7

HCID 313Hydrochloric AcidHCID 750GlycineHCID 5234Sodium ChlorideHCID 8359Isatoic AnhydrideHCID 14798Sodium HydroxideHCID 691752,4-DimethoxybenzaldehydeHCID 11042399(2,4-Dimethoxy-benzylamino)-acetic acid

Produkt 2

HCID 11042399(2,4-Dimethoxy-benzylamino)-acetic acidHCID 217643143,4-dihydro-4-(2,4-dimethoxybenzyl)-2H-1,4-benzodiazepine-2,5(1H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N-(2,4-dimethoxybenzyl)glycine is prepared by the reaction of glycine with 2,4-dimethoxybenzaldehyde in the presence of sodium hydroxide, reduction with palladium-on-carbon in methanol and subsequent neutralisation with 2 N hydrochloric acid. The aqueous solution obtained is concentrated. 41.9 g of this mixture of N-(2,4-dimethoxybenzyl)-glycine and sodium chloride are stirred at 110° C. for 1.5 hours in 300 ml of dimethyl sulphoxide with 23.18 g (142 mmol) of isatoic acid anhydride. The mixture is poured into ca 2 liters of water and stirred for 0.5 hour. The separated crystals are filtered off under suction, washed with water and dried. After recrystallisation from ethyl acetate, there is obtained 3,4-dihydro-4-(2,4-dimethoxybenzyl)-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 151°-152.5° C.

Aufarbeitung

  1. customThe aqueous solution obtained
  2. concentrationis concentrated
  3. filtrationThe separated crystals are filtered off under suction
  4. washwashed with water
  5. customdried
  6. customAfter recrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-39334f19e71744d793e29b729d245f50
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346032

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