Tin tetrachloride → HCID 178480624, Verbindung

HRID 392610

Reaktionsgleichung

Reaktionsgleichung von HRID 392610
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][C:11]([O:13]CC)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:19][C:18]=1[C:30]#[N:31].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:29][N:26]1[CH2:25][CH2:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]3[C:18](=[C:30]([NH2:31])[C:10]([C:11]([N:16]=3)=[O:13])=[C:2]3[NH:1][C:5]4[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=4)[NH:3]3)[CH:19]=2)[CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 24287Tin tetrachlorideHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 219285192-Amino-5-(4-methyl-1-piperazinyl)benzonitrile

Produkt 1

HCID 178480624HCID 178480624, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 2-benzimidazol-2-ylacetate (1.1 eq) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 eq) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 eq) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80° C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rf 1.65 minutes.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureUpon cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. additionNaOH (3 M) was added to the solid
  6. filtrationThe solid was filtered
  7. washwashed sequentially with H2O, CH2Cl2, and acetone
  8. custompurified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-f2e1585b151d40ecb98e8ce46ec367ea
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800760B2

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