Thiourea → Ethyl 2-amino-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylate

HRID 2282288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282288
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C>[NH2:21][C:19]1[S:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:18]=1

Komponenten

4

Edukt 2

HCID 2723790ThioureaHCID 58094874Ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate

Produkt 1

HCID 58094863Ethyl 2-amino-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate (5.14 g, 15.1 mmol) in ethanol (90 mL) was added thiourea (1.26 g, 16.6 mmol) and the solution was stirred at reflux for 2 hours. The reaction was allowed to cool to room temperature, then the solvent was evaporated in vacuo. Column chromatography was performed to yield the title compound (4.79 g, 99%). LCMS: (AA) ES+, 319. 1H NMR (300 MHz, d1-chloroform) δ: 8.11 (br s, 2H), 7.52-7.33 (m, 3H), 4.24-4.16 (m, 2H), 1.23-1.17 (m, 3H).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a132a0328ab49a5b2ae116a70d85a91
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139589B2

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