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

HRID 490325Notes

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>>[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

Reactant 3

HCID 10796Cesium carbonate

HCID 18430Epibromohydrin

HCID 231766N-(2-Hydroxyphenyl)benzamide

Product 1

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

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 acetontrile 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

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

Sources & evidence

ORD record: ord-dde0bc5b1ff24d04b27a6d6413b66d36
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528156B2

Reaction notes

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