Pyridine → 1,3-benzothiazole-2-carbonitrile

HRID 2044137ノート

反応式

HRID 2044137 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([NH2:12])=O.N1C=CC=CC=1.O=P(Cl)(Cl)Cl>CCOC(C)=O.CCCCCC>[C:10]([C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)#[N:12]

参加物

6

反応物 3

HCID 1049PyridineHCID 24813Phosphorus oxychloride2 回HCID 6385612-benzothiazolecarboxamide

生成物 1

HCID 6385601,3-benzothiazole-2-carbonitrile収率 95%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

Benzothiazole-2-carboxamide 8 (0.61 mmol, 0.1 g) was dissolved in anhydrous pyridine (0.080 mol, 6.5 ml) and stirred under N2 at 0° C. The temperature of the reaction was dropped to 0° C. during dropwise addition of POCl3 (0.015 mol, 1.4 ml). The solution immediately changed from clear to a pale pink coloring with addition of POCl3. After 20 min, the acetone/ice bath was removed and the reaction was stirred at RT for 2 h further. The tan/brown-colored reaction was then transferred to a larger reaction flask containing 10 ml EtOAc at 0° C. The reaction was quenched by the dropwise addition of water. The organic product 10 was washed with water, extracted with EtOAc, and concentrated in vacuo to yield a light yellow/orange product. TLC analysis (3 Hexane: 2 EtOAc) and Agilent HPLC displayed 100% conversion to the desired product (single peak at 10.5 min). The compound was used in the subsequent step without purification (95% yield). ESI-MS: m/z calcd for C8H4N2S 161.01 (M+H)+, 160.86 found (100%). (see LC/MS spectra of FIG. 19A and NMR spectra of FIG. 19B).

後処理

  1. customthe acetone/ice bath was removed
  2. stirringthe reaction was stirred at RT for 2 h further
  3. customThe tan/brown-colored reaction
  4. customwas then transferred to a larger reaction flask
  5. customThe reaction was quenched by the dropwise addition of water
  6. washThe organic product 10 was washed with water
  7. extractionextracted with EtOAc
  8. concentrationconcentrated in vacuo
  9. customto yield a light yellow/orange product

出典と根拠

ORDレコード
ord-227e9043efb04fc1ae84f814bd0e0836
出典データセット
uspto-grants-2013_11
特許番号
US08586759B2

反応ノート

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