p-Toluenesulfonic acid → 1-Isopropylsulfonyl-2-amino-6-(alpha-aminocarbonylmethylenebenzyl)benzimidazole

HRID 904830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 904830
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27](O)([CH2:34][C:35]([NH2:37])=[O:36])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:39])(=[O:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27](=[CH:34][C:35]([NH2:37])=[O:36])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:39])(=[O:16])=[O:17])([CH3:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 204777191-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-aminocarbonylmethylbenzyl)benzimidazole

Produkt 1

HCID 47132911-Isopropylsulfonyl-2-amino-6-(alpha-aminocarbonylmethylenebenzyl)benzimidazoleAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 3.0 g. of p-toluenesulfonic acid and 3.0 g. of 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-aminocarbonylmethylbenzyl)benzimidazole (prepared as described in Example 23) in 100 ml. of chloroform was heated at reflux for four hours. The reaction mixture then was cooled, washed with aqueous sodium bicarbonate solution and with water, dried, and the solvent was removed by evaporation under reduced pressure. Crystallization of the product thus formed from tetrahydrofuran afforded 1.1 g. of trans-1-isopropylsulfonyl-2-amino-6-(α-aminocarbonylmethylenebenzyl)benzimidazole, M.P. 218°-219° C. Yield 35%, and 1.0 g. of the corresponding cis-isomer, M.P. 211°-212° C., yield 32%.

Aufarbeitung

  1. temperatureat reflux for four hours
  2. temperatureThe reaction mixture then was cooled
  3. washwashed with aqueous sodium bicarbonate solution and with water
  4. customdried
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customCrystallization of the product
  7. customthus formed from tetrahydrofuran
  8. customafforded 1.1 g

Quellen und Nachweise

ORD-Eintrag
ord-3eb1a86485fc4bccb5870f8ec1ad44fd
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04420479

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