Water → N-(2-chloro-5-nitrophenyl)-3,4-dimethoxybenzamide

HRID 991418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991418
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[Cl:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH2:17].O>N1C=CC=CC=1>[Cl:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH:17][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 226912-Chloro-5-nitroanilineHCID 77070Veratroyl chloride

Produkt 1

HCID 3551001N-(2-chloro-5-nitrophenyl)-3,4-dimethoxybenzamideAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3,4-Dimethoxybenzoyl chloride (2 g) was added to a stirred suspension of 2-chloro-5-nitroaniline (1.72 g) in pyridine (10 ml) at 20° C. The reaction mixture was heated to 100° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was poured into water (100 ml). The resulting precipitate was collected, washed with water and dried. The solid was triturated under methylene chloride (20 ml) to give N-(2-chloro-5-nitrophenyl)-3,4-dimethoxybenzamide (1.2 g), m.p. 231-232° C.; NMR Spectrum: (DMSOd6) 3.82 (s, 6H), 7.08 (d, 1H), 7.62 (m, 1H), 7.82 (d, 1H), 8.08 (m, 1H), 8.54 (d, 1H), 10.07 (m, 1H);

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried
  5. customThe solid was triturated under methylene chloride (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-be5cac2653734e61a10a60d8b32c5330
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465455B1

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