2-Aminophenol → 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

HRID 7735

Reaktionsgleichung

Reaktionsgleichung von HRID 7735
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:17][CH3:18])[C:15]=1[CH3:16])[C:10]([OH:12])=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].[CH:27](N(C(C)C)CC)(C)C>C1COCC1>[CH3:18][O:17][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[CH3:16])[C:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])=[O:12]

Komponenten

6

Edukt 4

HCID 58012-AminophenolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 37644863,5-Dimethoxy-4-methylbenzoic acid

Produkt 1

HCID 25993393,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Thionyl chloride (10 mL) and 3,5-dimethoxy-4-methylbenzoic acid (1.0 g, 5.1 mmol) was refluxed under argon until no starting material was observed by TLC. After cooling reaction mixture to rt, concentrated mixture in vacuo. The resulting brown oil was added to a mixture of 2-aminophenol (580 mg, 5.3 mmol), diisopropylethyl amine (1.1 mL, 6.3 mmol) and THF (40 mL) at 0° C. and then brought to rt overnight. After concentrating mixture in vacuo, the resulting brown oil was purified by flash chromatography on silica gel, using a gradient elution from 1:9 EtOAc:hexanes to 1:1 EtOAc:hexanes. This afforded the desired intermediate, 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide, as a colorless solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. customreaction mixture to rt
  3. concentrationconcentrated mixture in vacuo
  4. concentrationAfter concentrating mixture in vacuo
  5. customthe resulting brown oil was purified by flash chromatography on silica gel
  6. washa gradient elution from 1:9 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-6aab020e505c4013a9621c93cb7e9ea8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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