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Triethylamine → (3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine

HRID 1161654
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HRID 1161654 반응식
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[NH2:19])[O:14][CH3:15].C(N(CC)CC)C.C(Cl)(Cl)[Cl:28].CCCCCC>>[Cl:28][C:12]1[CH:11]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=2)[CH:17]=[CH:16][C:13]=1[O:14][CH3:15]
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참가 물질

5

반응물 4

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 4074322-Chloro-4-methoxyanilineHCID 21585165Chloroform hexane

생성물 1

HCID 58626087(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine수율 22%

실험 절차

To a solution of 2,4,6-trichloro-pyrimidine (0.29 g, 1.58 mmol) in 1:1 chloroform-hexane (10 mL) was added 3-chloro-p-anisidine (0.5 g, 3.1 mmol) at 25° C. with stirring. To this was added triethylamine (0.22 mL, 1.59 mmol) at 25° C. and the mixture was heated and refluxed for 7 hours under nitrogen atmosphere. The mixture was then concentrated under vacuum, diluted with cold water (30 mL) and extracted with ethyl acetate (2×60 mL). The organic layers were collected, combined, washed with brine (30 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The crude product thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to afford the desired compound. Yield: 22%.

후처리

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 7 hours under nitrogen atmosphere
  3. concentrationThe mixture was then concentrated under vacuum
  4. additiondiluted with cold water (30 mL)
  5. extractionextracted with ethyl acetate (2×60 mL)
  6. customThe organic layers were collected
  7. washwashed with brine (30 mL)
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customThe crude product thus obtained
  11. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-be9ab0e62d56432f96749a77f95e855d
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07820654B2

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