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

HRID 630385노트

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HRID 630385 반응식
[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]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 5102883Chloro-isopropyl-dimethylsilaneHCID 55277042(4-Amino-5-chloro-2-methoxyphenyl)methanol2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3059ad39c35c425c99e98cab15a03848
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315463B2

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