Dimethylformamide → 2-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 1667677

Reaktionsgleichung

Reaktionsgleichung von HRID 1667677
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[CH3:18][O:19][CH:20]([O:31][CH3:32])[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23](F)[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:23]2[CH:22]=[C:21]([CH:20]([O:31][CH3:32])[O:19][CH3:18])[CH:26]=[CH:25][C:24]=2[N+:27]([O-:29])=[O:28])=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateHCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzene

Produkt 1

HCID 866428042-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl esterAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.250 g (1 mmole) of 2-amino-4-phenyl-thiazole-5-carboxylic acid ethyl ester (V.1), 0.215 g (1 mmole) of 4-dimethoxymethyl-2-fluoro-1-nitro-benzene, 0.488 g (1.5 mmole) of cesium carbonate and 5 mL of dimethylformamide was heated at 100 degrees overnight. The cooled mixture was diluted with 30 mL of water and then extracted three times with 20 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexanes (gradient 0:100-10:90) to give 0.240 g of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VIA a) as an orange solid.

Aufarbeitung

  1. temperaturewas heated at 100 degrees overnight
  2. extractionextracted three times with 20 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with ethyl acetate-hexanes (gradient 0:100-10:90)

Quellen und Nachweise

ORD-Eintrag
ord-209deecfd88e4b9cae5e5829a02b08b4
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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