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

HRID 1281480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281480
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C@@H:13]2[CH2:15][O:14]2)[C:5]=1[NH2:6])([O-])=O.[O:16]1CCC[CH2:17]1>[Ni]>[O:14]1[CH2:15][C@H:13]1[CH2:12][O:11][C:7]1[C:5]2[NH:6][C:17](=[O:16])[NH:1][C:4]=2[CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

2-Nitro-6-[(2S)oxiranylmethoxy]aniline (0.20 g, 0.96 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL). Excess Raney Ni was added and the mixture hydrogenated under an atmosphere of hydrogen overnight. The mixture was filtered through a Celite pad. To the anhydrous tetrahydrofuran solution was added with cooling anhydrous N,N-diisopropylethylamine (0.365 mL) followed by phosgene in toluene (0.525 mL). The solvent was partially removed and the title compound collected by filtration (0.10 g, 0.49 mmol).

Aufarbeitung

  1. filtrationThe mixture was filtered through a Celite pad
  2. additionTo the anhydrous tetrahydrofuran solution was added with cooling anhydrous N,N-diisopropylethylamine (0.365 mL)
  3. customThe solvent was partially removed
  4. filtrationthe title compound collected by filtration (0.10 g, 0.49 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-51b81c6308fa4afca1ba7eaba9a08c09
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451814B1

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