Diethylcarbamoyl chloride → 6-(Propan-2-yl)pyridine-2-carbonitrile

HRID 471194노트

반응식

HRID 471194 반응식
C[Si]([C:5]#[N:6])(C)C.[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N+:11]=1[O-])([CH3:9])[CH3:8].C(N(CC)C(Cl)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:7]([C:10]1[N:11]=[C:12]([C:5]#[N:6])[CH:13]=[CH:14][CH:15]=1)([CH3:9])[CH3:8]

참가 물질

6

반응물 4

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 131720791-Oxo-2-(propan-2-yl)-1lambda~5~-pyridine

생성물 1

HCID 219927776-(Propan-2-yl)pyridine-2-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trimethylsilyl cyanide (1.53 mL) was added to a solution of 2-isopropylpyridine 1-oxide (example 85, step b) (1.3 g) in DCM (40 mL) and the resulting mixture was stirred for 5 min. Diethylcarbamoyl chloride (1.2 mL) was added and the mixture stirred for 3 days. An aqueous solution of potassium carbonate (10%, 40 mL) was added and the mixture stirred for 10 min. The layers were separated and the aqueous phase extracted with DCM (2×40 mL). The combined organic solutions were washed with brine (40 mL), dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 3:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 1.23 g.

후처리

  1. stirringthe mixture stirred for 3 days
  2. stirringthe mixture stirred for 10 min
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with DCM (2×40 mL)
  5. washThe combined organic solutions were washed with brine (40 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customPurification
  10. washeluting with 3:1 isohexane
  11. additionThe fractions containing product
  12. customevaporated

출처 및 근거

ORD 기록
ord-57b376b5797a4bc4bc60c372bbc6a37d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

반응 노트

불러오는 중…