Potassium Phosphate, Tribasic → 5-bromo-N,N-dimethyl-2-(2-oxo-oxazolidin-3-yl)-benzamide

HRID 1865656Notes

Reaction equation

HRID 1865656 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].[O:14]1[CH2:18][CH2:17][NH:16][C:15]1=[O:19].[C@H]1(N)CC[C@H](N)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH2:17][CH2:18][O:14][C:15]2=[O:19])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 739492-OxazolidinoneHCID 524394945-bromo-2-iodo-N,N-dimethylbenzamideHCID 178511674HCID 178511674, compound

Product 1

HCID 579757195-bromo-N,N-dimethyl-2-(2-oxo-oxazolidin-3-yl)-benzamideYield 65%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A microwave vial was charged with 5-bromo-2-iodo-N,N-dimethyl-benzamide (200 mg, 0.74 mmol), 2-oxazolidinone (77.4 mg, 0.89 mmol), copper(I)-iodide (70.5 mg, 0.04 mmol), trans-1,4-cyclohexanediamine (84.6 mg, 0.74 mmol), and potassium phosphate (377.2 mg, 1.78 mmol) and degassed dioxane (2 ml) added. The reaction mixture was irradiated to 150° C. for 1 hour in a microwave reactor. The solvent was evaporated and the resulting solid purified by silica gel chromatography to give 5-bromo-N,N-dimethyl-2-(2-oxo-oxazolidin-3-yl)-benzamide as a white solid (150 mg, 65% yield). MS: m/z 315.4 (M+H+).

Workup

  1. customdegassed dioxane (2 ml)
  2. additionadded
  3. customThe reaction mixture was irradiated to 150° C. for 1 hour in a microwave reactor
  4. customThe solvent was evaporated
  5. customthe resulting solid purified by silica gel chromatography

Sources & evidence

ORD record
ord-7869476136a5448fbaf3890bd3c4178a
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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