Methanol → Methyl 2-(2-hydroxy-4,5-diMethoxybenzaMido)thiazole-4-carboxylate

HRID 78702

Reaktionsgleichung

Reaktionsgleichung von HRID 78702
[OH:1][C:2]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:3]=1[C:4]([O:6]C1C=CC=CC=1)=O.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=1.CO>C1(C)C(C)=CC=CC=1>[CH3:30][O:29][C:27]([C:25]1[N:26]=[C:22]([NH:21][C:4](=[O:6])[C:3]2[CH:13]=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:2]=2[OH:1])[S:23][CH:24]=1)=[O:28]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 53424183Phenyl 2-hydroxy-4,5-dimethoxybenzoate

Produkt 1

HCID 86711696Methyl 2-(2-hydroxy-4,5-diMethoxybenzaMido)thiazole-4-carboxylateAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

In 250 mg of xylene were suspended 250 mg of phenyl 2-hydroxy-4,5-dimethoxybenzoate (3a) and 144 mg of methyl 2-amino-1,3-thiazole-4-carboxylate (4a) in a stream of argon, which was then heated to reflux (at 140° C.) for 7 hours. The reaction was not completed. After cooling, methanol was added, followed by stirring for one hour. The precipitated crystal was collected by filtration and dried under reduced pressure at 60° C. to provide 170 mg of the same compound (5a) as that of Example 4 at a yield of 55%.

Aufarbeitung

  1. temperaturewas then heated
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystal was collected by filtration
  4. customdried under reduced pressure at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-627ac6ae4aef42b99e2567cbc7caaca5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841461B2

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