Lawesson's reagent → Ethyl 5-amino-1,3-thiazole-4-carboxylate

HRID 408833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408833
[CH:1]([NH:3][C@H:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]#[N:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1C=CC=CC=1>[NH2:6][C:5]1[S:21][CH:1]=[N:3][C:4]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 86619658Ethyl N-formyl-3-nitriloalaninate

Produkt 1

HCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Ethyl N-formyl-3-nitriloalaninate (11.22 g, 71.86 mmol) is dissolved in anhydrous benzene (220 mL). Following the addition of Lawesson's reagent (14.53 g, 35.93 mmol), the suspension is refluxed for 24 h. Most of the solvent is removed in vacuo, and the viscous red residue is absorbed on silica gel and loaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50). The title compound is obtained as yellow solids. 1H NMR (400 MHz, CDCl3) 7.87 (1H, s), 7.26 (1 H, s), 6.01 (2H, broad s), 4.38 (2H, q), 1.41 (3H, t).

Aufarbeitung

  1. temperaturethe suspension is refluxed for 24 h
  2. customMost of the solvent is removed in vacuo
  3. customthe viscous red residue is absorbed on silica gel
  4. washloaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50)

Quellen und Nachweise

ORD-Eintrag
ord-7eaf2e0f23d94fa7a31be1214a2b96db
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759361B2

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