Hydrochloric Acid → 5-(4-hydroxy-phenylsulfanyl methyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

HRID 1348957

Reaktionsgleichung

Reaktionsgleichung von HRID 1348957
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([O:15]C(=O)C)[N:8](C(=O)C)[C:9]=1[CH2:10]Br)=[O:4].[SH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=[O:15])[NH:8][C:9]=1[CH2:10][S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 865974912-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl ester

Produkt 1

HCID 711950995-(4-hydroxy-phenylsulfanyl methyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4c (640 mg, 2 mmol) in 20 mL of MeOH was added 4-mercaptophenol (380 mg, 3.0 mmol) and K2CO3 (550 mg, 4.0 mmol). The solution was stirred at rt for 6 h. 20 mL of water was then added and 2 mL of 1N HCl was carefully added. This aqueous solution was extracted with Et2O. The aqueous solution was then concentrated and the residue was first dissolved in 5 mL of MeOH and the diluted with 50 mL of CH2Cl2. Filtration and concentration provided 5-(4-hydroxy-phenylsulfanyl methyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 4d (440 mg, 80%). MS (ESI+) (M+AcN+1)=322.

Aufarbeitung

  1. extractionThis aqueous solution was extracted with Et2O
  2. concentrationThe aqueous solution was then concentrated
  3. dissolutionthe residue was first dissolved in 5 mL of MeOH
  4. additionthe diluted with 50 mL of CH2Cl2
  5. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-f06bd47ddf5a4ffd959dcfce4faeb1a0
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211671B2

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