Diisopropylethylamine → 1-Methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

HRID 2288363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288363
[CH2:1]([N:4]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]([C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:16])[C:12]([CH2:14]Cl)=[N:13][C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3].[C:26]([C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1)#[N:27].C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:1]([N:4]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]([C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:16])[C:12]([CH2:14][S:34][C:31]3[CH:32]=[CH:33][C:28]([C:26]#[N:27])=[CH:29][CH:30]=3)=[N:13][C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5850584-ThiobenzonitrileHCID 184123762-Chloromethyl-1-methylbenzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Produkt 1

HCID 184123961-Methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g (4.1 mMol) of 2-chloromethyl-1-methyl-benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)-amide and 0.65 g (4.8 mMol) of p-cyanothiophenol was heated in 10 ml of dimethylformamide and 10 ml of diisopropylethylamine for 1 hour to 100° C. The solvent was distilled off in vacuo, the crude product was dissolved in 30 ml ethyl acetate, washed with 30 ml water, and after concentration purified by flash chromatography (silica gel; methylene chloride/ethanol (49:1 to 19:1). Yield: 1.5 g (79% of theory) of brown oil, Rf value: 0.65 (silica gel; ethyl acetate/ethanol/ammonia =90:10:1)

Aufarbeitung

  1. distillationThe solvent was distilled off in vacuo
  2. dissolutionthe crude product was dissolved in 30 ml ethyl acetate
  3. washwashed with 30 ml water
  4. concentrationafter concentration
  5. custompurified by flash chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0dcfb3d3ef814acb9c43201f0483fddd
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087380

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