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N,N'-Dimethylethylenediamine → Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate

HRID 715988
ノート
印刷プレビュー

反応式

HRID 715988 の反応式
CNCCNC.Br[C:8]1[C:9]([N+:25]([O-:27])=[O:26])=[C:10]([C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].[NH:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.[Cu]I>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19]([NH:18][C:15]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([N+:25]([O-:27])=[O:26])[C:8]([N:28]2[CH2:32][CH2:31][CH2:30][C:29]2=[O:33])=[CH:17][CH:16]=1)=[O:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 70982880Methyl 3-bromo-6-(2,2-dimethylpropionyl-amino)-2-nitrobenzoate2 回

生成物 1

HCID 70982623Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate収率 17.8%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A solution of N,N′-dimethylethylenediamine (1.72 g) in toluene (15 mL) was added to a mixture of methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-nitro-benzoate (Intermediate 58, 1.72 g), pyrrolidin-2-one (0.489 g), copper(I) iodide (0.091 g) and potassium carbonate (1.32 g) and the mixture was stirred and heated under nitrogen at 110° C. for 5 hours. After cooling, the mixture was diluted with water and ethyl acetate and the organic phase was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-80% to give methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate (0.310 g) as an off-white solid.

後処理

  1. temperatureAfter cooling
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-80%

出典と根拠

ORDレコード
ord-48bcd428ce9c4c60affb03714d8d0fb0
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187494B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート