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Ethanolamine → 1-(4-Chloro-phenyl)-2-(2-hydroxy-ethylamino)-1-(4-iodo-phenyl)-ethanol

HRID 45546
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HRID 45546 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH2:18]([CH2:20][NH2:21])[OH:19].C(N(CC)CC)C>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)([OH:9])[CH2:10][NH:21][CH2:20][CH2:18][OH:19])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 593172172-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

생성물 1

HCID 593319671-(4-Chloro-phenyl)-2-(2-hydroxy-ethylamino)-1-(4-iodo-phenyl)-ethanol수율 99.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane (0.60 g, 1.68 mmol), ethanolamine (0.5 mL, 8.3 mmol) and triethylamine (0.5 mL, 3.6 mmol) in iso-propanol (5 mL) was maintained at 50° C. for 72 hours then concentrated in vacuo. The residue was taken up in ethyl acetate and washed with saturated potassium carbonate solution/water (1:9). The aqueous phase was extracted a second time with ethyl acetate, then the combined extracts were washed with brine, dried (MgSO4), filtered and concentrated to give the title compound (701 mg, quantitative); LCMS (PS-A2) Rt 2.29 min [M+H]+ 418, [M−H2O+H]+ 400.

후처리

  1. concentrationthen concentrated in vacuo
  2. washwashed with saturated potassium carbonate solution/water (1:9)
  3. extractionThe aqueous phase was extracted a second time with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-974860b0b1ac4481b8f2061acf6e8a2c
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541461B2

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