Cesium carbonate → N-Methyl-2-oxiranylmethoxy-benzamide

HRID 490326

Reaction equation

HRID 490326 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Br>C(#N)C>[CH3:7][NH:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[O:1][CH2:18][CH:20]1[CH2:21][O:22]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 74624N-Methylsalicylamide

Product 1

HCID 22386982N-Methyl-2-oxiranylmethoxy-benzamideYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-Hydroxy-N-methyl-benzamide (0.5 g, 3.31 mmol prepared according to Cohen, Seth M et al J. Am. Chem. Soc., (1998), 120(25), 6277-6286.) and cesium carbonate (2.16 g, 6.62 mmol) in acetonitrile was added epibromohydrin (0.274 ml, 3.31 mmol). The mixture was heated at 50° C. for 2 hours and then after cooling to room temperature partitioned between water (50 ml) and dichloromethane (100 ml). The dichloromethane was dried and evaporated. Chromatography (EtOAc) gave 0.43 g (64%) of the product as a solid.

Workup

  1. temperatureafter cooling to room temperature
  2. custompartitioned between water (50 ml) and dichloromethane (100 ml)
  3. dry with materialThe dichloromethane was dried
  4. customevaporated

Sources & evidence

ORD record
ord-2ff0570bf3414a08a7b66e6291d26fb3
Source dataset
uspto-grants-2009_05
Patent number
US07528156B2

Linked notes

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