Water → HCID 18667959, compound

HRID 1060235Notes

Reaction equation

HRID 1060235 reaction equation
[H-].[Na+].[N:3]1[O:7][N:6]=[C:5]2[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:4]=12.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.O>CN(C)C=O>[N:3]1[O:7][N:6]=[C:5]2[C:8]([O:12][CH2:13][CH:15]3[O:17][CH2:16]3)=[CH:9][CH:10]=[CH:11][C:4]=12

Participants

6

Reactant 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 135542663HCID 135542663, compound

Product 1

HCID 18667959HCID 18667959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (620 mg; 60% oil dispersion) was added in portions to benzofurazan-4-ol (1.74 g) in dimethylformamide (30 ml). The mixture was heated at 50° C. for 30 min. Epibromohydrin (1.6 ml) was added and the mixture was heated at 60° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4, and evaporated. The residue was chromatographed on silica gel (50% ethyl acetate/hexane) to give 1-(4-benzofurazanyloxy)-2,3-epoxypropane (1.6 g), mp 75° C.

Workup

  1. temperaturethe mixture was heated at 60° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5f99c7b31b954cfc934af00dd5122071
Source dataset
uspto-grants-2003_02
Patent number
US06521755B1

Reaction notes

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