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2-Bromoethanol → N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline

HRID 356223
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HRID 356223 반응식
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].C(N(CC)C(C)C)(C)C.Br[CH2:21][CH2:22][OH:23]>O>[CH2:1]([N:3]([CH2:21][CH2:22][OH:23])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]
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참가 물질

5

반응물 3

HCID 108982-Bromoethanol2회HCID 81531Diisopropylethylamine2회HCID 117456564-bromo-N-ethylaniline

생성물 1

HCID 18941473N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline수율 69.5%

시약·촉매·용매 1

HCID 962Water용매

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온도
125 °C

실험 절차

17.3 g (86.7 mmols) of N-ethyl-4-bromoaniline, 22.7 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 9.64 ml (1.5-fold equivalent weight) of 2-bromoethanol were mixed, and the mixture obtained was heated at 125° C. for 2 hours in an atmosphere of argon. Next, to the reaction solution obtained, 1.5 ml (0.1-fold equivalent weight) of diisopropylethylamine and 0.64 ml (0.1-fold equivalent weight) of 2-bromoethanol were added, and the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography developing system (chloroform) to obtain 14.7 g of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline (yield: 69.5%; a colorless oily liquid).

후처리

  1. customthe mixture obtained
  2. customNext, to the reaction solution obtained
  3. customthe mixture obtained
  4. temperaturewas heated at 125° C. for 3 hours in an atmosphere of argon
  5. customobtained
  6. extractionwhich was then extracted with ethyl acetate
  7. customThe organic layer obtained
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-007123975d5847128a691b561d3559d1
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05834575

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