4-(Bromoacetyl)benzonitrile → 2-amino-5-(4-cyano-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 133028

Reaktionsgleichung

Reaktionsgleichung von HRID 133028
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH2:6][C:7](=[NH:9])[NH2:8])[CH3:3].[O-]CC.[Na+].Br[CH2:16][C:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)=O>C(O)C>[CH2:2]([O:4][C:5]([C:6]1[CH:16]=[C:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[NH:9][C:7]=1[NH2:8])=[O:10])[CH3:3]

Komponenten

5

Edukt 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 2723922Sodium ethoxideHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Produkt 1

HCID 691589182-amino-5-(4-cyano-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A mixture of 42.53 g (0.255 mol) carbamimidoyl-acetic acid ethyl ester hydrochloride in 70 ml absolute ethanol is treated at 0 to 5° C. with 95.3 ml of a 21% sodium ethoxide solution in ethanol (0.255 mol) and stirred 5 min at 0 to 5° C. 4-Bromoacetyl-benzonitrile (28.6 g, 0.128 mol) is then added in portions over 20 min at 0 to 5° C. Stirring is continued at this temperature for 5 min then the ice bath is removed and the yellow suspension is stirred over night at RT. The solid is filtered off, washed with ethanol and ether and re-suspended in 450 ml actonitrile. The mixture is heated for 5 min under reflux, filtered while still hot and then cooled in an ice bath. The title compound is collected by succion and dried. Flash chromatography (dichtoromethane/ethyl acetate mixture) of the mother liquors gives an additional crop of the title compound as a yellow solid; m.p. 228-229° C.; MS-ES+: (M+H)+=254.

Aufarbeitung

  1. stirringStirring
  2. waitis continued at this temperature for 5 min
  3. customthe ice bath is removed
  4. stirringthe yellow suspension is stirred over night at RT
  5. filtrationThe solid is filtered off
  6. washwashed with ethanol and ether
  7. temperatureThe mixture is heated for 5 min
  8. temperatureunder reflux
  9. filtrationfiltered while still hot and
  10. temperaturethen cooled in an ice bath
  11. customThe title compound is collected by succion
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8e8d411034a346a3b031889df9058a94
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390805B2

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