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

HRID 428551

반응식

HRID 428551 반응식
[CH:1]1[CH:6]=[N+:5]([O-])[CH:4]=[C:3]([CH2:8][C:9]#[N:10])[CH:2]=1.C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O>C(Cl)Cl>[C:9]([CH2:8][C:3]1[C:4]([C:15]#[N:16])=[N:5][CH:6]=[CH:1][CH:2]=1)#[N:10]

참가 물질

5

반응물 3

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

생성물 1

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrile수율 66%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of (1-oxy-pyridin-3-yl)-acetonitrile (10 g, 75 mmol) in anhydrous CH2Cl2 under a nitrogen atmosphere was added trimethylsilylcyanide (10.95 mL, 82 mmol) and dimethylcarbamoylchloride (7.55 mL, 82 mmol). The reaction mixture was stirred at room temperature for 72 hours and then concentrated. EtOAc (100 mL) was added to the residue and the organic phase was washed with 1 M NaOH (150 mL), dried over Na2SO4, filtered and concentrated. The resulting solid was purified by column chromatography (50% EtOAc/hexanes) affording 7.08 g (66%) of a yellow solid: mp 48-51° C.; MS(+)APCI m/z 144 [M+H]+.

후처리

  1. concentrationconcentrated
  2. additionEtOAc (100 mL) was added to the residue
  3. washthe organic phase was washed with 1 M NaOH (150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was purified by column chromatography (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c2d975a92a1f4a4eac22a07a0a3142ad
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313126B1

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