Phosphorus oxychloride → 6-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic Acid Ethyl Ester

HRID 1293087

Reaktionsgleichung

Reaktionsgleichung von HRID 1293087
[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH2:11][C:12](=O)[N:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:9]2=[N:8][C:7]=1[C:24]([F:27])([F:26])[F:25])=[O:5])[CH3:2].P(Cl)(Cl)([Cl:30])=O>>[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([Cl:30])[N:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:9]2=[N:8][C:7]=1[C:24]([F:27])([F:26])[F:25])=[O:5])[CH3:2]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 207802246-oxo-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester

Produkt 1

HCID 207802236-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic Acid Ethyl Ester

Versuchsvorschrift

A solution of 6-oxo-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (3.04 g, 6.137 mol) in phosphorus oxychloride (70 mL) was heated at 150° C. for 72 h. The excess of phosphorus oxychloride was removed under reduced pressure, the residue was dissolved in saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (5×50 mL). The combined organic extracts were dried with MgSO4. The solvent was removed under reduced pressure and the crude product was dried under pump vacuum overnight. Yield—1.192 g (38%). LC/MS: tR=2.17 min., MS: [M+H]=400.

Aufarbeitung

  1. customThe excess of phosphorus oxychloride was removed under reduced pressure
  2. dissolutionthe residue was dissolved in saturated aqueous solution of sodium bicarbonate (100 mL)
  3. extractionextracted with ethyl acetate (5×50 mL)
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. dry with materialthe crude product was dried under pump vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-0fd37881bb694df78d0fee1904be6d04
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238699B2

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