Dicyclohexylcarbodiimide → 2-{[2-Aminoacetamido-5-chloro-alpha-(2-fluorophenyl)benzylidene]amino}ethanol

HRID 2397789

Reaktionsgleichung

Reaktionsgleichung von HRID 2397789
C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:17][CH2:18][C:19](O)=[O:20].[NH2:22][C:23]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:24]=1[C:25](=[N:33][CH2:34][CH2:35][OH:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32]>CN(C)C=O.O.O1CCCC1>[NH2:17][CH2:18][C:19]([NH:22][C:23]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:24]=1[C:25](=[N:33][CH2:34][CH2:35][OH:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[O:20]

Komponenten

7

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 22316Glycine HydrochlorideHCID 233227792-{[2-Amino-5-chloro-alpha-(2-fluorophenyl)benzylidene]amino}ethanol

Produkt 1

HCID 133415892-{[2-Aminoacetamido-5-chloro-alpha-(2-fluorophenyl)benzylidene]amino}ethanolAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4.5g of N,N'-dicyclohexylcarbodiimide in 100ml of dimethylformamide is added a solution of 2.2g of glycine hydrochloride in 2.2ml of water in a period of about 30 seconds under stirring and ice-cooling. Immediately a solution of 3.2g of 2-{[2-amino-5-chloro-α-(2-fluorophenyl)benzylidene]amino}ethanol in 10ml of tetrahydrofuran is added dropwise to the above solution and the mixture is stirred for further 3 hours. After completion of the reaction, the reaction mixture is treated by the same manner as described in the Example 1, yielding 1.7g of the desired product melting at 128°-132° C.

Aufarbeitung

  1. temperatureice-cooling
  2. stirringthe mixture is stirred for further 3 hours
  3. customAfter completion of the reaction
  4. additionthe reaction mixture is treated by the same manner

Quellen und Nachweise

ORD-Eintrag
ord-d46dc407160746ce91c68278008aa4d7
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04022832

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