Oxalyl chloride → Ethyl 2-(4-(3,4-dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoate

HRID 2099960

Reaktionsgleichung

Reaktionsgleichung von HRID 2099960
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[Cl:17].C(Cl)(=O)C(Cl)=O.[NH2:29][C:30]1[CH:40]=[CH:39][C:38]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:37][C:31]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:29][C:30]2[CH:40]=[CH:39][C:38]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:37][C:31]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:14])=[CH:10][C:9]=1[Cl:17]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57796887Ethyl 2-amino-5-phenoxybenzoateHCID 577968974-(3,4-Dimethoxybenzyloxy)-3-chlorobenzoic acid

Produkt 1

HCID 57796889Ethyl 2-(4-(3,4-dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1B (200 mg, 0.62 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and treated with several drops of DMF. Oxalyl chloride was added dropwise over 10 minutes. The resulting solution was stirred for 10 minutes, and then concentrated to dryness. The resulting solid was dissolved in CH2Cl2 (10 mL) and treated with ethyl 2-amino-5-phenoxybenzoate (144 mg, 0.56 mmol) and diisopropylethylamine (130 μL, 0.74 mmol). The reaction was stirred at room temperature for 3 hours and then concentrated to afford 1C as a white solid.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting solid was dissolved in CH2Cl2 (10 mL)
  3. stirringThe reaction was stirred at room temperature for 3 hours
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-69fd503af22c4d219c7e558793126094
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569725B2

Verknüpfte Notizen

Wird geladen…