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Ethylenediamine → HCID 57548171, 화합물

HRID 1993909
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HRID 1993909 반응식
C[Al](C)C.[CH2:5]([NH2:8])[CH2:6][NH2:7].C(O[C:12](=O)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)C>C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:12]2[NH:7][CH2:6][CH2:5][N:8]=2)=[CH:16][CH:17]=1
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참가 물질

5

반응물 3

HCID 3301EthylenediamineHCID 10921830Ethyl 3-(4-chlorophenyl)propanoateHCID 16682925Trimethylaluminum

생성물 1

HCID 57548171HCID 57548171, 화합물수율 50.9%

시약·촉매·용매 1

HCID 1140Toluene용매4회

실험 절차

To dry toluene (4 ml) under an inert atmosphere at 0° C. was added a toluene solution of trimethylaluminium (2.45 ml, 4.89 mmol, 2 M solution). A solution of ethylenediamine (0.30 ml, 4.89 mmol) in toluene (1.5 ml) was then added dropwise and the reaction mixture was then allowed to warm to room temperature and stirred for 1 h at this temperature before being re-cooled to 0° C. To this mixture was added dropwise a solution of 3-(4-chloro-phenyl)-propionic acid ethyl ester (0.52 g, 2.45 mmol) in toluene (3 ml). The reaction mixture was then heated at 95° C. for 45 min and then cooled first to room temperature and finally to 0° C. The mixture was quenched by dropwise addition of methanol (1 ml) and when all gas evolution had ceased the mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in ether to yield a white solid (0.26 g, 50%) which was collected by filtration; MS (ISP): 211.0, 209.2 ([M+H]+.).

후처리

  1. temperaturebefore being re-cooled to 0° C
  2. temperatureThe reaction mixture was then heated at 95° C. for 45 min
  3. temperaturecooled first to room temperature and finally to 0° C
  4. customThe mixture was quenched by dropwise addition of methanol (1 ml) and when all gas evolution
  5. additionwas diluted with water
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated in ether

출처 및 근거

ORD 기록
ord-076653fa99bd42c1bd0ca6531b22e581
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652055B2

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