3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → Methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylate

HRID 237349

Reaktionsgleichung

Reaktionsgleichung von HRID 237349
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=[O:4].[F:11][C:12]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:13]=1[NH2:14]>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[C:9]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([I:19])=[CH:18][C:12]=2[F:11])=[CH:8][S:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 2

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 1856942-Fluoro-4-iodoaniline

Produkt 1

HCID 66617580Methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl-4-oxo-tetrahydro-thiophene-3-carboxylate (5.75 g, 35.9 mmol) and 2-fluoro-4-iodo-aniline (9.4 g, 40.9 mmol) were heated to reflux in a mixture of ethanol (25 mL) and acetic acid (0.3 mL) for 18 hours. The solution was cooled to room temperature, filtered and the solid product dried in vacuo to provide methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylate (5.70 g, 42% yield). MS (EI) for C12H11FINO2S: 380 (MH+).

Aufarbeitung

  1. filtrationfiltered
  2. customthe solid product dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b0c61ca66c2446087e7accda5ed23b4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642584B2

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