Ethylamine → 2-chloro-N-ethyl-4-thiazolecarboxamide

HRID 368687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368687
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7](Cl)=[O:8])[N:6]=1.ClC1S[CH:13]=[C:14](C(O)=O)[N:15]=1.S(Cl)(Cl)=O.C(N)C>O.CN(C=O)C>[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:15][CH2:14][CH3:13])=[O:8])[N:6]=1

Komponenten

7

Edukt 4

HCID 6341EthylamineHCID 24386Thionyl ChlorideHCID 218030262-Chloro-1,3-thiazole-4-carboxylic acidHCID 450815362-Chloro-1,3-thiazole-4-carbonyl chloride

Produkt 1

HCID 186300282-chloro-N-ethyl-4-thiazolecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Chloro-4-thiazolecarboxylic acid chloride (prepared from 2-chloro-4-thiazolecarboxylic acid, thionyl chloride and a catalytic amount of DMF) was reacted with 70% ethylamine in water to yield 2-chloro-N-ethyl-4-thiazolecarboxamide. This compound was reacted with TMSCl using the method of step c of Example 248. Purification by flash chromatography with 3% ethyl acetate-hexane gave 2.5 g of the title compound as a light yellow oil in 55.6% yield. nD26 1.5313.

Quellen und Nachweise

ORD-Eintrag
ord-62242aad9e3642caa94b6286245bf4fc
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133252

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