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2-(Benzo[d]thiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrile → 1,3-Benzothiazol-2-yl(pyrimidin-4-yl)acetonitrile

HRID 2377593
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HRID 2377593 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].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[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]=[CH:15][N:14]=1)[C:11]#[N:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 3952292-(Benzo[d]thiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrileHCID 517045Sodium Acetate

생성물 1

HCID 179068071,3-Benzothiazol-2-yl(pyrimidin-4-yl)acetonitrile수율 13.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

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온도
70 °C

실험 절차

To a solution of 1 (0.1 g, 0.35 mmol) in acetic acid was added sodium acetate (29 mg, 0.35 mmol) and palladium on charcoal (20 mg). The suspension was heated up to 70° C. under hydrogen at 3.5 bar for 3 h. After cooling to r.t., the suspension was filtered through celite and the acetic acid evaporated. The bright yellow powder was taken up in ethyl acetate and aqueous sodium hydroxide 10%. After 3 extractions the organic phases were thoroughly washed with brine then dried over MgSO4 and concentrated to dryness. After purification by preparative HPLC and drying under vacuum at 50° C., 12 mg (13%) of the title compound were obtained as a yellow powder.

후처리

  1. temperatureAfter cooling to r.t.
  2. filtrationthe suspension was filtered through celite
  3. customthe acetic acid evaporated
  4. extractionAfter 3 extractions the organic phases
  5. washwere thoroughly washed with brine
  6. dry with materialthen dried over MgSO4
  7. concentrationconcentrated to dryness
  8. customAfter purification by preparative HPLC
  9. customdrying under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-eb1e3da77b1a47679dbc3f0f04feb804
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07470686B2

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