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Dimethylcarbamoyl Chloride → 6-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carbonitrile

HRID 1528373
ノート
印刷プレビュー

反応式

HRID 1528373 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[CH:12][CH:11]=[CH:10][N+:9]=2[O-])=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)CC)C.CN(C)C(Cl)=O.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:20]#[N:22])[CH:11]=[CH:12][C:13]=2[O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][CH:3]=1
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

6

反応物 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 666786042-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide

生成物 1

HCID 666786996-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carbonitrile収率 59.3%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
90 °C

実験手順

To a solution of 25 g 2-(4-chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide in 500 mL acetonitrile, 9.23 g triethylamine and 10.73 g dimethylcarbamoylchlorid were added. After 5 minutes at room temperature, 27.88 g trimethylsilylcyanid was added. The reaction mixture was stirred at 90° C. over 15 h. The reaction mixture was partitioned between water and ethyl acetate; then extracted. The organic phase was washed with brine; then dried over MgSO4 and purified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate 2:1 to yield 15.30 g (59.26%) of the title compound as light yellow solid, MS 285.1 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionthen extracted
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried over MgSO4
  5. custompurified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate 2:1

出典と根拠

ORDレコード
ord-e453291991294a24a66c3827673e2be1
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090599B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート