2-Amino-4-(4-aminophenyl)thiazole → 4-Amino-benzylidene-hydantoin

HRID 1637932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637932
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[NH:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1)([O-])=O.NC1SC=C(C2C=CC(N)=CC=2)N=1>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[NH:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 6055642-Amino-4-(4-aminophenyl)thiazoleHCID 46859054-Nitro-benzylidene-hydantoin

Produkt 1

HCID 538516234-Amino-benzylidene-hydantoin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 3 g (12.9 mmol) of crude 4-nitro-benzylidene-hydantoin, melting point 300° C. (prepared as described in Example 6 under (a)) in 50 ml 80% acetic acid are added 3 g of iron powder at 100°. After 30 minutes the mixture is filtered over kieselguhr and the filtrate is evaporated down in vacuo. The evaporation residue is divided between EtOac and dilute aqueous ammonia solution; before the separation of the phases the mixture is filtered once more through kieselguhr. The organic phase is washed with water, dried, filtered and evaporated down in vacuo. The yellow foam obtained (0.80 g; 30.6% of theory) predominantly contains 4-amino-benzylidene-hydantoin (A) (Rf =0.55), but no 4-amino-benzyl-hydantoin (B) (Rf =0.48), according to DC (silica gel; toluene/EtOac/EtOH (4:2:1)).

Aufarbeitung

  1. filtrationAfter 30 minutes the mixture is filtered over kieselguhr
  2. customthe filtrate is evaporated down in vacuo
  3. custombefore the separation of the phases the mixture
  4. filtrationis filtered once more through kieselguhr
  5. washThe organic phase is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated down in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d71ca5a8497c40c99cb6f9c6366ccaa6
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043254

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