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4-Methoxyphenol → 1,3-Benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile

HRID 2377592
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HRID 2377592 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:14]=1)[C:11]#[N:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 3952292-(Benzo[d]thiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrile

생성물 1

HCID 99514801,3-Benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile수율 51.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

To a solution of 1 (0.300 g, 1.05 mmol) in DMSO (7 ml) were added 4-methoxyphenol (0.261 g, 2.1 mmol) and cesium carbonate (1.7 g, 5.25 mmol) and the suspension was shaken at 100° C. for 8 days. After cooling to r.t., the suspension was poured onto ice/water and the product was extracted with AcOEt. The organic phases were washed with water then brine, dried over MgSO4 and concentrated to dryness. The residue was triturated in hot EtOH then filtered off and dried under vacuum at 50° C. overnight, affording 202 mg (51%) of the title compound.

후처리

  1. temperatureAfter cooling to r.t.
  2. additionthe suspension was poured onto ice/water
  3. extractionthe product was extracted with AcOEt
  4. washThe organic phases were washed with water
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe residue was triturated in hot EtOH
  8. filtrationthen filtered off
  9. customdried under vacuum at 50° C. overnight

출처 및 근거

ORD 기록
ord-755d2af574174fa7b5e1339829c2fd63
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07470686B2

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