Phosphorus oxychloride → 3-{[4-Chloro-5-fluoro-2-(methoxymethoxy)benzoyl]amino}thiophene-2-carboxamide

HRID 225458

Reaktionsgleichung

Reaktionsgleichung von HRID 225458
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[C:15]([F:16])=[CH:14][C:10]([C:11]([O-:13])=O)=[C:9]([O:17][CH2:18][O:19][CH3:20])[CH:8]=1.[Li+].[NH2:22][C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([NH2:30])=[O:29]>N1C=CC=CC=1>[Cl:6][C:7]1[C:15]([F:16])=[CH:14][C:10]([C:11]([NH:22][C:23]2[CH:27]=[CH:26][S:25][C:24]=2[C:28]([NH2:30])=[O:29])=[O:13])=[C:9]([O:17][CH2:18][O:19][CH3:20])[CH:8]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 5189933-Aminothiophene-2-carboxamideHCID 69077744Lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate

Produkt 1

HCID 690746473-{[4-Chloro-5-fluoro-2-(methoxymethoxy)benzoyl]amino}thiophene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

n-butyllithium was added to a diethyl ether solution of 1-bromo-4-chloro-5-fluoro-2-(methoxymethoxy)benzene in a dry ice-acetone bath and stirred for one hour. The reaction solution was added to a mixture of dry ice and diethyl ether and stirred for two hours to give lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate. Phosphorus oxychloride was added to a mixture of the obtained lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate, 3-aminothiophene-2-carboxamide and pyridine in a MeOH ice bath and stirred for one hour to give 3-{[4-chloro-5-fluoro-2-(methoxymethoxy)benzoyl]amino}thiophene-2-carboxamide.

Quellen und Nachweise

ORD-Eintrag
ord-b6f1d9a9f6e644cfa86965f3b6902012
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557112B2

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