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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
ノート
印刷プレビュー

反応式

HRID 2377593 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-eb1e3da77b1a47679dbc3f0f04feb804
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07470686B2

反応ノート

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