Sulfuryl chloride → 3-Chloropyrazine-2-carbonitrile

HRID 16704

反応式

HRID 16704 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[N:8].S(Cl)([Cl:12])(=O)=O>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:12][C:3]1[C:2]([C:7]#[N:8])=[N:1][CH:6]=[CH:5][N:4]=1

参加物

5

反応物 2

HCID 24648Sulfuryl chlorideHCID 73172Pyrazinecarbonitrile

生成物 1

HCID 2924653-Chloropyrazine-2-carbonitrile収率 47.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

Pyrazine-2-carbonitrile (26.36 g) is dissolved in toluene (187 ml)/N,N-dimethylformamide (19 ml), and thereto is added dropwise sulfuryl chloride (135 g) under ice-cooling. After completion of addition, the reaction solution is warmed to room temperature gradually and stirred overnight. The toluene layer is separated and the residual red oil is extracted with diethyl ether. The organic layers are combined, cooled with ice, and after pouring thereto ice-water, neutralized by adding saturated aqueous sodium hydrogen carbonate solution. The organic layer is separated, and aqueous layer is extracted with diethyl ether. The organic layers are combined, washed with water, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (16.58 g).

後処理

  1. temperaturecooling
  2. additionAfter completion of addition
  3. customThe toluene layer is separated
  4. extractionthe residual red oil is extracted with diethyl ether
  5. temperaturecooled with ice
  6. additionafter pouring
  7. additionby adding saturated aqueous sodium hydrogen carbonate solution
  8. customThe organic layer is separated
  9. extractionaqueous layer is extracted with diethyl ether
  10. washwashed with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated
  13. customto remove the solvent under reduced pressure
  14. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-0130e7830dff4585b90743179ee76437
出典データセット
uspto-grants-2010_06
特許番号
US07737161B2

関連ノート

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