Imidazole → 4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline

HRID 630385ノート

反応式

HRID 630385 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.N1C=CN=[CH:14]1.Cl[Si:19]([CH:22]([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O>[Si:19]([O:10][CH2:9][C:5]1[C:4]([O:11][CH3:12])=[CH:3][C:2]([NH2:1])=[C:7]([Cl:8])[CH:6]=1)([C:22]([CH3:24])([CH3:14])[CH3:23])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 795ImidazoleHCID 5102883Chloro-isopropyl-dimethylsilaneHCID 55277042(4-Amino-5-chloro-2-methoxyphenyl)methanol2 回

生成物 1

HCID 671456574-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of (4-amino-5-chloro-2-methoxyphenyl)methanol (intermediate 38; 1.5 g, 0.008 mol) in dimethylformamide (35 mL) was added imidazole (1.7 g, 0.02 mol). The mixture was cooled to 0° C. and chloro(isopropyl)dimethylsilane (2.5 g, 0.01 mol) was added dropwise. The reaction was stirred overnight at room temperature. The solvent was removed and the crude was partitioned between water and hexane, the organic layer was washed with water, sodium bicarbonate 4% and brine, dried, filtered and evaporated to dryness. The crude obtained was purified by column chromatography with silica gel, eluting with hexane/ethyl acetate (from 8/1 to 4/1). The title compound was obtained as a yellow solid (58%).

後処理

  1. customThe solvent was removed
  2. customthe crude was partitioned between water and hexane
  3. washthe organic layer was washed with water, sodium bicarbonate 4% and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude obtained
  8. customwas purified by column chromatography with silica gel
  9. washeluting with hexane/ethyl acetate (from 8/1 to 4/1)

出典と根拠

ORDレコード
ord-3059ad39c35c425c99e98cab15a03848
出典データセット
uspto-grants-2016_04
特許番号
US09315463B2

反応ノート

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