Cesium carbonate → N-(2-Oxiranylmethoxy-phenyl)-benzamide

HRID 1072496Notes

Reaction equation

HRID 1072496 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Br>C(#N)C>[O:27]1[CH2:26][CH:25]1[CH2:23][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 231766N-(2-Hydroxyphenyl)benzamide

Product 1

HCID 22386962N-(2-Oxiranylmethoxy-phenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(2-Hydroxy-phenyl)-benzamide (0.81 g, 3.80 mmol), and cesium carbonate (1.61 g, 4.94 mmol) in acetonitrile was added epibromohydrin (0.63 ml, 7.60 mmol). After 4 hours the reaction mixture was partitioned between dichloromethane and water. After evaporation of the organic solvent the residue was crystallised from petroleum ether and diethyl ether yielding (0.741 g, 73%).

Workup

  1. customAfter 4 hours the reaction mixture was partitioned between dichloromethane and water
  2. customAfter evaporation of the organic solvent the residue
  3. customwas crystallised from petroleum ether and diethyl ether yielding (0.741 g, 73%)

Sources & evidence

ORD record
ord-84e815b8a9ab43fab3bff02ec36f91fb
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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