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

HRID 395973Notes

Reaction equation

HRID 395973 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2b254919b8b2497cb6844c3131f61b84
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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