Hydrochloric Acid → HCID 86642809, Verbindung

HRID 1667702

Reaktionsgleichung

Reaktionsgleichung von HRID 1667702
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:16][C:17]3[CH:22]=[C:21]([CH:23](OC)[O:24]C)[CH:20]=[CH:19][C:18]=3[N+:28]([O-:30])=[O:29])[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:16][C:17]3[CH:22]=[C:21]([CH:23]=[O:24])[CH:20]=[CH:19][C:18]=3[N+:28]([O-:30])=[O:29])[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 866428084-(3-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 86642809HCID 86642809, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3.2 g (7.1 mmole) of 4-(3-chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.2a), 30 mL of 2M hydrochloric acid and 5 mL of dimethylformamide was stirred at 60 degrees for 3 hours. The mixture was cooled and then concentrated under reduced pressure. The residue was taken up in 100 mL of dichloromethane and washed once with 100 mL of saturated sodium bicarbonate solution, once with 50 mL of brine, and then dried over anhydrous sodium sulfate. The mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (50:50) to give 2.5 g of 4-(3-chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.2b).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. washwashed once with 100 mL of saturated sodium bicarbonate solution, once with 50 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexanes-ethyl acetate (50:50)

Quellen und Nachweise

ORD-Eintrag
ord-640a78a52e50403895e8ac020d81bcdd
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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