2,4-Dimethoxybenzoic acid → HCID 19040985, Verbindung

HRID 1683816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683816
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH:14]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])[CH3:15].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:17]([CH:14]([CH3:16])[CH3:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7]

Komponenten

6

Edukt 4

HCID 70522,4-Dimethoxybenzoic acidHCID 13032N-IsopropylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 19040985HCID 19040985, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 2,4-dimethoxybenzoic acid (4.31 g, 23.7 mmol) in 35 mL of dichloromethane is treated with N-isopropylaniline (3.07 mL, 21.33 mmol), hydroxybenzotriazole (3.2 g, 23.7 mmol), and 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (4.54 g, 23.7 mmol). This solution is stirred at room temperature for 18 hours and the resulting solution is partitioned between ethyl acetate and 1N hydrochloride solution. The organic layer is washed with water, dried over sodium sulfate and concentrated. The resulting material is purified by chromatography on silica gel (150 g) with 40-60% ethyl acetate/hexane as the eluent to afford 2,4-dimethoxy-N-(1-methylethyl)-N-phenylbenzamide as a colorless foam.

Aufarbeitung

  1. customthe resulting solution is partitioned between ethyl acetate and 1N hydrochloride solution
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting material is purified by chromatography on silica gel (150 g) with 40-60% ethyl acetate/hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-13bb4d4a8f154d5c91c0ed15e1522d29
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639768

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