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

HRID 1805360ノート

反応式

HRID 1805360 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-76d820331c864ce989db863d5708d70c
出典データセット
uspto-grants-2013_01
特許番号
US08354443B2

反応ノート

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