N,N'-Dimethylethylenediamine → Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate

HRID 1805360Notes

Reaction equation

HRID 1805360 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6]([Br:11])[CH:5]=1.[O:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([N:15]2[CH2:16][CH2:17][O:13][C:14]2=[O:18])[CH:7]=[C:6]([Br:11])[CH:5]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 21942573Methyl 3-bromo-5-iodobenzoate

Product 1

HCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 3-bromo-5-iodo-benzoic acid methyl ester (682 mg, 2 mmol), oxazolidin-2-one (191 mg, 2.2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 3-bromo-5-(2-oxo-oxazolidin-3-yl)-benzoic acid methyl ester (480 mg, 80%) which was used for next step without further purification.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-76d820331c864ce989db863d5708d70c
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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