Dicyclohexylcarbodiimide → HCID 178451273, Verbindung

HRID 358557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358557
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(N)=S)=[CH:4][N:3]=1.[C:12]([O:16][C:17](=[O:20])[CH2:18][NH2:19])([CH3:15])([CH3:14])[CH3:13].[CH:21]1([N:27]=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[C:7]([C:21](=[NH:27])[NH:19][CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 151417Glycine tert-butyl esterHCID 47003394N-(6-Chloropyridin-3-yl)thiourea

Produkt 1

HCID 178451273HCID 178451273, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.2 g (6.4 mmol) of 2-chloro-5pyridylthiourea, 1 g (7.68 mmol) of glycine tert-butyl ester and 1.45 g (7.04 mmol) of dicyclohexylcarbodiimide in 30 ml of ethyl acetate is heated for 2.5 hr at 60° C. The dicyclohexylthiourea precipitate formed is eliminated by filtration. The filtrate is concentrated to dryness The product obtained is taken up in 20 ml of dichloromethane and then extracted with a 0.25 N aqueous hydrochloric acid solution (4 × 30 ml). The acid solution is then neutralized with a 1 N sodium hydroxide solution, and thereafter is extracted with dichloromethane (3× 20 ml), thus permitting 0.65 g (yield 36%) of tert-butyl N-[2-chloro-5-aminopyridyl(imino)methyl]-2-aminoethanoate to be obtained in the form of an oil.

Aufarbeitung

  1. customThe dicyclohexylthiourea precipitate
  2. customformed
  3. filtrationis eliminated by filtration
  4. concentrationThe filtrate is concentrated to dryness The product
  5. customobtained
  6. extractionextracted with a 0.25 N aqueous hydrochloric acid solution (4 × 30 ml)
  7. extractionis extracted with dichloromethane (3× 20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7a7633551c794599858e8b35d9ef8166
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997667

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