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

HRID 1393053Notes

Reaction equation

HRID 1393053 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 strred 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 crystallized from petroleum ether and diethyl ether yielding the title compound (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
  3. customthe residue was crystallized from petroleum ether and diethyl ether yielding the title compound (0.741 g, 73%)

Sources & evidence

ORD record
ord-93754ee0ff5b45c7850124d116cca57f
Source dataset
uspto-grants-2008_03
Patent number
US07345063B2

Reaction notes

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