Potassium Carbonate → 4-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1862761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862761
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[N+](C1C=C(S(O[CH2:25][C@H:26]2[O:28][CH2:27]2)(=O)=O)C=CC=1)([O-])=O.[C:29](=O)([O-])[O-:30].[K+].[K+]>CC(=O)CC>[O:28]1[CH2:27][C@H:26]1[CH2:25][O:11][C:3]1[C:2]2[NH:1][C:29](=[O:30])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41154952-Amino-3-Nitrophenol

Produkt 1

HCID 105124504-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-3-nitrophenol (12.0 g, 77.8 mmol), (S)-(+)-glycidyl 3-nitrobenzenesulfonate (20.18, 77.8 mmol) and potassium carbonate (11.8 g, 77.8 mmol) in 2-butanone (100 mL) was heated at reflux for 18 hours essentially as described for Procedure A. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 2:1 hexane-diethyl ether) to yield the title compound (4.30 g, 20.46 mmol).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours essentially
  3. customThe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 2:1 hexane-diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-284f87a35e954f4d8cd2fadfb607a5e2
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06537994B2

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