Sodium hydride → Thiazolo[4,5-b]pyridine,2-[(2,2,2-trifluoroethyl)thio]-

HRID 1279239ノート

反応式

HRID 1279239 の反応式
[H-].[Na+].[S:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]1[SH:12].C1(C)C=CC(S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O)=CC=1>CN(C)C=O>[F:25][C:24]([F:27])([F:26])[CH2:23][S:12][C:4]1[S:3][C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[CH:9][CH:10]=2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 178527821HCID 178527821、化合物

生成物 1

HCID 22385774Thiazolo[4,5-b]pyridine,2-[(2,2,2-trifluoroethyl)thio]-収率 77.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

A mixture of sodium hydride (60% suspension in oil, 0.72 g, 0.03 mol) in N,N-dimethylformamide is cooled to 0° C., treated dropwise with a solution of thiazolo[4,5-b]pyridine-2-thiol (5.0 g, 30 mmol) in N,N-dimethylformamide, stirred for 30 minutes, treated with a solution of 2,2,2-trifluoroethyl p-toluenesulfonate (3.81 g, 15 mmol) in N,N-dimethylformamide, heated to and stirred at 110° C. for 6 hours, and poured into an ice/water mixture. The resultant aqueous mixture is extracted with diethyl ether. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using an ethyl acetate/hexanes solution gives the title product as a light yellow liquid (2.91 g, 39% yield).

後処理

  1. temperatureheated to and
  2. stirringstirred at 110° C. for 6 hours
  3. extractionThe resultant aqueous mixture is extracted with diethyl ether
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue

出典と根拠

ORDレコード
ord-0a40d219543d41dbaf753419cdfcd12a
出典データセット
uspto-grants-2002_09
特許番号
US06448262B1

反応ノート

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