Potassium Carbonate → 2-Chlorophenyl-(2-pyrimidinyl)acetonitrile

HRID 48972

反応式

HRID 48972 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]([C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:5]#[N:6]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 76112(o-Chlorophenyl)acetonitrile2 回

生成物 1

HCID 123729682-Chlorophenyl-(2-pyrimidinyl)acetonitrile収率 70.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of 2-chlorobenzyl cyanide (4.50 g, 0.297 mol), potassium carbonate (6.84 g, 0.0495 mol) and dimethylformamide is stirred 30 minutes at 100° C. and treated dropwise with a solution of 2-chloropyrimidine (2.30 g, 0.0201 mol) in dimethylformamide. The resultant mixture is stirred overnight at 100° C. and treated with additional 2-chlorobenzyl cyanide (1.54 g, 0.0102 mol). The mixture is stirred several more hours at 100° C., cooled and diluted with water. The mixture is extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant brown oil is chromatographed on silica gel with ethyl acetate-hexanes to afford the title compound as a brown oil (3.25 g, 70.8%) which is identified by NMR spectral analysis.

後処理

  1. stirringThe mixture is stirred several more hours at 100° C.
  2. temperaturecooled
  3. extractionThe mixture is extracted three times with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant brown oil is chromatographed on silica gel with ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-2c9d7adb2ed548a2970388d8922ff6b3
出典データセット
uspto-grants-2004_03
特許番号
US06706663B2

関連ノート

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