Hydrochloric Acid → 2-(5-Formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 1667678

Reaktionsgleichung

Reaktionsgleichung von HRID 1667678
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH:18](OC)[O:19]C)[CH:15]=[CH:14][C:13]=2[N+:23]([O-:25])=[O:24])=[N:8][C:7]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5])[CH3:2].Cl>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][C:13]=2[N+:23]([O-:25])=[O:24])=[N:8][C:7]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 866428042-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 866428052-(5-Formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl esterAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 0.089 g (0.2 mmole) of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1a), 2 mL of actonitrile and 0.5 mL of 1 M hydrochloric acid was stirred at 60 degrees for 30 minutes. The mixture was concentrated under reduced pressure. The residue was diluted with 5 mL of saturated sodium bicarbonate and extracted twice with 20 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.080 g of 2-(5-formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1b) as an orange oil. The crude was carried to the next step reaction without further purification.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with 5 mL of saturated sodium bicarbonate
  3. extractionextracted twice with 20 mL of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-db49e020fbc747b282916d2477dc0549
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

Verknüpfte Notizen

Wird geladen…