5-Amino-2-methylphenol → 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide

HRID 2190442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190442
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:14][CH2:13]1)#[N:11].C(Cl)(=O)C(Cl)=O.C(=O)([O-])O.[Na+]>O.O1CCCC1.CN(C)C=O>[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=2)=[O:19])[CH2:13][CH2:14]1)#[N:11]

Komponenten

8

Edukt 4

HCID 178185-Amino-2-methylphenolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Produkt 1

HCID 673125573-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamideAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Using 5-amino-2-methylphenol (6.00 g, 48.5 mmol), 3-(1-cyanocyclopropyl)benzoic acid (6.00 g, 48.5 mmol) produced in Example A1(iii), oxalyl chloride (6.40 mL, 73.0 mmol), N,N-dimethylformamide (40 μL), tetrahydrofuran (250 mL), sodium hydrogencarbonate (6.20 g, 73.0 mmol) and water (60 mL) as starting materials, and in the same manner as in Example A32(i), the title compound (12.4 g, 87%) was obtained as a white powder. The title compound was washed with a mixed solvent of ethyl acetate and hexane.

Quellen und Nachweise

ORD-Eintrag
ord-9d7c02803abc4c4691af04383fdd01f5
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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