2-Aminobenzaldehyde → 2-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide

HRID 270698

Reaktionsgleichung

Reaktionsgleichung von HRID 270698
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>S(Cl)(Cl)=O.ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20])=[O:15]

Komponenten

6

Edukt 2

HCID 682552-AminobenzaldehydeHCID 542654372,6-Dichloro-3-nitrophenylacetic acid

Produkt 1

HCID 598338822-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamideAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of (2,6-dichloro-3-nitro-phenyl)-acetic acid (0.90 g, 3.35 mmol) in thionyl chloride (15 mL) is refluxed for one hour. The solvent is removed by concentration and dry toluene is added to thoroughly remove thionyl chloride. To the solution of acid chloride in dry dichloromethane (30 mL) is added (drop-wise) a solution of 2-aminobenzaldehyde (0.365 g, 3.02 mmol) in dichloromethane (5.0 mL). The mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product (0.94 g, 88.6%).

Aufarbeitung

  1. customThe solvent is removed by concentration and dry toluene
  2. additionis added to thoroughly remove thionyl chloride
  3. washwashed with saturated K2CO3 and brine
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-85921cc9266e4e75939cb8df0dbc30ea
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

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