Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-mercaptobenzimidazole-7-carboxylate

HRID 1977374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977374
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:29](=S)(OCC)[S-:30].[Na+]>C(O)C>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:13]2[C:3]3[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=3[N:1]=[C:29]2[SH:30])=[CH:16][CH:17]=1)#[N:28]

Komponenten

4

Edukt 2

HCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 23690437Sodium ethylxanthate

Produkt 1

HCID 178468776Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-mercaptobenzimidazole-7-carboxylateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 3-amino-2-[(2′-cyanobiphenyl-4-yl)-methyl]aminobenzoate (5.6 g) and sodium O-ethyl dithiocarbonate (7.3 g) in ethanol (50 ml) was heated for 8 hours under reflux. The reaction mixture was concentrated and the residue was dissolved in water. The solution was adjusted to pH 3-4 with hydrochloric acid. Precipitating crystals were collected by filtration, followed by recrystallization from ethanol to afford yellow crystals (5.0 g, 80%), m.p. 225-227° C.

Aufarbeitung

  1. temperaturewas heated for 8 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water
  5. customPrecipitating crystals
  6. filtrationwere collected by filtration
  7. customfollowed by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5569aa333c1943bd8ba954f23b62be7b
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232334B1

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