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Imidazole → 5-[3-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]thiazol-2-amine

HRID 524418
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HRID 524418 반응식
[NH2:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:5][N:6]=1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[Si:20]([O:15][CH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][C:4]1[S:3][C:2]([NH2:1])=[N:6][CH:5]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86669548[3-(2-Aminothiazol-5-yl)oxyphenyl]methanol

생성물 1

HCID 866695505-[3-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]thiazol-2-amine수율 39.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

[3-(2-aminothiazol-5-yl)oxyphenyl]methanol (1.70 g, 7.575 mmol), tert-butyldimethylchlorosilane (1.38 g, 9.189 mmol), and imidazole (0.625 g, 9.189 mmol) was taken in 20 mL of dry DMF and heated at 60° C. for overnight. TLC showed consumption of starting material. The reaction mixture was cooled to room temperature and poured into water and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get the crude product which was purified by column chromatography using 5-30% ethyl acetate in hexanes to get pure title compound (0.998 g).

후처리

  1. customconsumption of starting material
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto get the crude product which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-d5a50fadec024ef3be2992115347627b
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340506B2

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