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

HRID 992072

반응식

HRID 992072 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-cf89a84d4e8e4c04b7d5e82db027f738
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465482B2

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