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

HRID 715988
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HRID 715988 반응식
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]
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참가 물질

9

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 70982880Methyl 3-bromo-6-(2,2-dimethylpropionyl-amino)-2-nitrobenzoate2회

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 962Water용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-48bcd428ce9c4c60affb03714d8d0fb0
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187494B2

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