Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

HRID 1269098노트

반응식

HRID 1269098 반응식
CO[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](O)=O)[CH:4]=1.C[Si](C#N)(C)C.CO[C:20]1[CH:25]=[CH:24][N+]([O-])=[CH:22][CH:21]=1.C[N:28](C)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:22]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:28])[CH:4]=1)[CH2:21][CH2:20][CH2:25][CH3:24]

참가 물질

7

반응물 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 707434-Methoxypyridine N-oxideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 20500994-Methoxypyridine-2-carboxylic acid

생성물 1

HCID 210760834-Pentyl-2-cyanopyridine수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

4-Methoxypyridine-2-carboxylic acid, compound 10(b) (R9=methoxy), was made employing Method P. To trimethylsilyl cyanide (0.95 g, 9.6 mmol), 4-methoxypyridine N-oxide (1 g, 8 mmol) in DCM (10 mL) was added, followed by dimethylcarbamoyl chloride (1.03 g, 9.6 mmol) in DCM (10 mL), dropwise. After stirring at room temperature overnight, sodium bicarbonate (100 mL, 10%) was added, and the organic layer was separated. The aqueous layer was extracted twice by DCM (50 mL each). The combined organic layer was dried over magnesium sulfate and the solvent was removed to obtain product, compound 10a (0.97 g, 90%):

후처리

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice by DCM (50 mL each)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. customthe solvent was removed

출처 및 근거

ORD 기록
ord-11db0f0b3eac45f280ac931cb2145e6a
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199105B2

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