Dimethylcarbamoyl Chloride → 3-(Cyanomethyl)pyridine-2-carbonitrile

HRID 369023

반응식

HRID 369023 반응식
[C:1]([CH2:3][C:4]1[CH:5]=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=1)#[N:2].C[Si](C)(C)[C:13]#[N:14].CN(C)C(Cl)=O>ClCCl>[C:13]([C:5]1[C:4]([CH2:3][C:1]#[N:2])=[CH:9][CH:8]=[CH:7][N:6]=1)#[N:14]

참가 물질

5

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 2431673-(Cyanomethyl)pyridin-1-ium-1-olate

생성물 1

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred suspension of 3-cyanomethylpyridine-N-oxide (30 g, 0.22 mol; for synthesis see Shigenobu Okuda, Michael M. Robison, J. Am. Chem. Soc. 81, 740 (1959)) in dichloromethane (200 ml) is added trimethylsilanecarbonitrile (26 g, 0.26 mol). To this suspension is added dimethylcarbamyl chloride (28 g, 0.26 mol). The mixture is stirred for 45 h. The solvent is removed and the residue dissolved in ethyl acetate. The solution is washed with 1 N NaOH and water and concentrated in vacuo. The product is purified by flash column chromatography on silica gel (15:2 toluene/acetone) affording the title compound. Mass M+H 144.1. Melting point 62-63° C.

후처리

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe solution is washed with 1 N NaOH and water
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by flash column chromatography on silica gel (15:2 toluene/acetone)

출처 및 근거

ORD 기록
ord-902b28c48d864fa98c2458152f224f06
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

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