3-(Trifluoromethyl)benzoic acid → N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 655791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655791
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1.O>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([C:11]([F:10])([F:21])[F:22])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Komponenten

7

Edukt 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1188893-Iodo-p-toluidine

Produkt 1

HCID 7925506N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-iodo-4-methylaniline (1.22 g, 5.25 mmol), 3-(trifluoromethyl)benzoic acid (0.95 g, 5 mmol), HOBt (0.68 g, 5 mmol), and EDCI (1.05 g, 5.5 mmol) in THF (20 mL) was stirred overnight at rt. Water was added and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (3:1 hexane/ethyl acetate) yielding the desired product.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated on a rotavap

Quellen und Nachweise

ORD-Eintrag
ord-3955adb1bd64479dba7c28a6b82e94ba
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071609B2

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