Hydrazine hydrate (1:1) → HCID 69419623, Verbindung

HRID 1766982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766982
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]=1[CH:11]=O)=[O:5])[CH3:2].O.[NH2:28][NH2:29]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:9]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:10]=1[CH:11]=[N:28][NH2:29])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 58760951HCID 58760951, Verbindung

Produkt 1

HCID 69419623HCID 69419623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-formyl-1H-imidazole-4-carboxylic acid ethyl ester (I-2e, 102 mg, 0.26 mmol), aqueous hydrazine hydrate (50% solution, 0.6 mmol) and glacial acetic acid (1 drop) was heated under reflux in toluene (3 ml) for 18 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The residue was partitioned between CH2Cl2 and sat'd aq. NaHCO3. The organic solution was dried and concentrated in vacuo. Purification using 2 mm chromatotron plates and a solvent gradient of 1:1 EtOAc/hexanes to 100% EtOAc provided the desired product I-2f (Rf=0.8, 100% EtOAc, 62 mg): +APCI MS (M+1) 403.1; 1H NMR (CD2Cl2) δ 1.40 (3H, t), 4.37 (2H, q), 5.60 (2H, br s), 7.10–7.14 (2H, m), 7.21–7.25 (3H, m), 7.29–7.33 (3H, m), 8.40 (1H, s).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2
  3. customThe organic solution was dried
  4. concentrationconcentrated in vacuo
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-b9f9201d8b744e54b3c40598b842075e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232823B2

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