2-Naphthylisothiocyanate → 5-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512526

Reaktionsgleichung

Reaktionsgleichung von HRID 512526
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].[N:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[C:9]=[S:10]>CCOC(C)=O>[NH2:7][C:6]1[S:10][C:9]([NH:8][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Komponenten

4

Edukt 2

HCID 742222-NaphthylisothiocyanateHCID 983412-Amino-2-cyanoacetamide

Produkt 1

HCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamideAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2-amino-2-cyanoacetamide (0.486 g, 2.70 mmol) in EtOAc (15 mL), was added 2-isothiocyanatonaphthalene (0.5 g, 2.70 mmol), and the mixture was refluxed for 30 min. The solvent was evaporated under reduced pressure, and the resulting crude residue was purified by silica gel column chromatography eluted with 2% MeOH in DCM to give 0.6 g (78% yield) of the titled compound.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting crude residue was purified by silica gel column chromatography
  4. washeluted with 2% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-e09bde594e424d9b9ddb00cffa647485
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102637B2

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