Water → 2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 1990992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1990992
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1.C(N([CH:23]([CH3:25])C)CC)(C)C.C([NH3+])C.[OH2:29].C[N:31]([CH:33]=[O:34])[CH3:32]>O1CCOCC1>[O:29]=[C:32]1[CH2:25][CH2:23][C:33](=[O:34])[N:31]1[O:15][C:14]([C:12]1[N:13]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[S:10][CH:11]=1)=[O:16]

Komponenten

7

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27439872-(2,3-dichlorophenyl)-1,3-thiazole-4-carboxylic AcidHCID 3427831Ethanaminium

Produkt 1

HCID 589249272-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl esterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid (4.1 g, 15 mmol) was dissolved in a mixture of 50 mL of DMF and 50 mL of dioxane. To this solution diisopropylethylamine (7.8 mL, 45 mmol) and ethanaminium, N-[(dimethylamino)[(2,5-dioxo-1-pyrrolidinyl)oxy]methylene]-N-methyl-, tetrafluoroborate(1-) (TSTU, Aldrich Inc.; 6.8 g, 22.5 mmol) was added. The reaction mixture was stirred at room temperature for 3 h after which 150 mL water was added and the organic layer was separated. The organic layer was extracted with 50 mL water twice, dried and concentrated. The crude mixture was washed with 100 mL isopropanol, to give 2-(2,3-dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (4.8 g, 87% yield) and used without further purification.

Aufarbeitung

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionThe organic layer was extracted with 50 mL water twice
  4. customdried
  5. concentrationconcentrated
  6. washThe crude mixture was washed with 100 mL isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-5b1a48f56d684c1f969be01d81dd89c9
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645773B2

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