Nitrogen → 3-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1015639

Reaktionsgleichung

Reaktionsgleichung von HRID 1015639
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:13][CH2:12]1)=[O:4].N#N.[Cl:22][C:23]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>ClC(Cl)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:13][CH2:12]1)[C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:23]=1[Cl:22])=[O:4]

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 666452,4-Dichlorobenzoyl chlorideHCID 207757643-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 207757633-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl esterAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (52 mg, 0.19 mmol) in dichloroethane (10 ml) in an atmosphere of N2 was added 2,4-dichlorobenzoyl chloride (45 mg, 0.21 mmol). The reaction mixture was stirred for 16 h at reflux. Then, the solvant was removed and the residue was purified by flash chromatography (8:2 Hexane/EtOAc) to obtain 85 mg (99%) of 3-[Cyclopropyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.64 ppm (d, 2H, Haro); 7.47 ppm (m, 2H, Haro); 7.44-7.33 ppm (m, 3H, Haro); 7.21-7.12 ppm (m, 2H, Haro); 3.89 ppm (s, 3H); 3.33 ppm (m, minor rotamer); 3.13 ppm (m, 1H, major rotamer) 1.01-0.49 ppm (m, 4H).

Aufarbeitung

  1. temperatureat reflux
  2. customThen, the solvant was removed
  3. customthe residue was purified by flash chromatography (8:2 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e048088dd3774af7ae50d7445af6a36c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985769B2

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