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

HRID 45546

反応式

HRID 45546 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-974860b0b1ac4481b8f2061acf6e8a2c
出典データセット
uspto-grants-2013_09
特許番号
US08541461B2

関連ノート

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