Potassium Cyanide → 1,3-benzothiazole-2-carbonitrile

HRID 1618088ノート

反応式

HRID 1618088 の反応式
[C-:1]#[N:2].[K+].Cl[C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.CCCCCCC.C(OCC)(=O)C>CS(C)=O>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)#[N:2]

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 119872-ChlorobenzothiazoleHCID 21899848Ethylacetate heptane

生成物 1

HCID 6385601,3-benzothiazole-2-carbonitrile収率 57.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A suspension of potassium cyanide (1.50 g, 23.0 mmol) in dimethylsulfoxide (DMSO, 100 mL) was prepared in a 1-L 3-necked flask fitted with a reflux condenser, a heating mantle and an internal temperature probe. The 2-chlorobenzothiazole (2.6 g, 2.0 mL, 15.3 mmol) was added to the reaction flask via pipet and the reaction was heated at 80° C. (internal temperature). The reaction was monitored periodically by TLC (9:1 heptane-ethyl acetate). After 5 hours the reaction appeared to be about 50% complete. After 17 hours the reaction was judged complete by TLC analysis. The reaction mixture was allowed to cool to room temperature and was then extracted with ether (5×100 mL). The extracts were dried over sodium sulfate and concentrated to give a yellow-orange solid. The crude solid was purified on silica gel (100 g) using 9:1 heptane-ethyl acetate. Fractions containing product were pooled and concentrated to give 1.4 g (57%) of the desired product as a yellow-orange solid. The structure was confirmed by 1H NMR analysis in DMSO-d6.

後処理

  1. customwas prepared in a 1-L 3-necked flask
  2. customfitted with a reflux condenser
  3. waitAfter 17 hours the reaction was judged complete by TLC analysis
  4. temperatureto cool to room temperature
  5. extractionwas then extracted with ether (5×100 mL)
  6. dry with materialThe extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a yellow-orange solid
  9. customThe crude solid was purified on silica gel (100 g)
  10. additionFractions containing product
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-7dc242f65fc9462a906d83c9c32cd762
出典データセット
uspto-grants-2014_07
特許番号
US08765969B2

反応ノート

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