Ammonia → Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate

HRID 569816

Reaktionsgleichung

Reaktionsgleichung von HRID 569816
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])O[C:8](=O)[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].BrC[C:18]([O:20][CH2:21][CH3:22])=[O:19].[NH3:23].Cl>CN(C)C=O>[C:6]([C:5]1[CH:12]=[CH:13][C:2]([Cl:1])=[CH:3][C:4]=1[NH:9][CH2:8][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:11])[NH2:23]

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 3291054-Chloroisatoic anhydride

Produkt 1

HCID 11780149Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 7-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (330 g) in N,N-dimethylformamide (3.3 l) was added sodium hydride (60% in mineral oil, 86.8 g) below 20° C. and the mixture was stirred at 5° C. for 30 minutes. To this solution was added ethyl bromoacetate (222 ml) at 10° C. over a 30-minute period and the resulting mixture was stirred at room temperature for 1.5 hours. To this reaction mixture was added 28% aqueous ammonia (696 ml) below 10° C. and the resulting mixture was stirred at 5° C. for 20 minutes. The mixture was poured into 1N hydrochloric acid (16.5 l). The precipitates were collected by filtration, and washed in turn with water (3 times) and diethyl ether to give ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate (360 g).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 1.5 hours
  2. stirringthe resulting mixture was stirred at 5° C. for 20 minutes
  3. filtrationThe precipitates were collected by filtration
  4. washwashed in turn with water (3 times) and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9a66eb8ff95041c1ae746444b1df9af3
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04734419

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