Dimethylcarbamoyl Chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 418047

반응식

HRID 418047 반응식
[C:1]1([C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si]([C:18]#[N:19])(C)(C)C.CN(C)C(Cl)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:18]([C:11]1[CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9][N:10]=1)#[N:19]

참가 물질

6

반응물 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

생성물 1

HCID 877584-Phenyl-2-pyridinecarbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-phenylpyridine N-oxide (5 g) in DCM (50 ml) was added at RT TMSCN (4 ml), and the solution was stirred for 5 min at RT. Then, dimethylcarbamoyl chloride (2.8 ml) was added at RT, and the resulting solution was stirred at RT for 48 h. To the reaction mixture was added a solution of aq. 10% K2CO3 (50 ml) and stirring was continued for 10 min. The phases were separated and the aq. layer extracted twice with DCM. The combined org. phases were dried over MgSO4 and evaporated off. Filtration over a plug of SiO2 (Hept/EA 8:2) gave 4.98 g of the desired compound.

후처리

  1. stirringthe resulting solution was stirred at RT for 48 h
  2. stirringstirring
  3. waitwas continued for 10 min
  4. customThe phases were separated
  5. extractionthe aq. layer extracted twice with DCM
  6. dry with materialphases were dried over MgSO4
  7. customevaporated off
  8. filtrationFiltration over a plug of SiO2 (Hept/EA 8:2)

출처 및 근거

ORD 기록
ord-b8a1245b0b204da9807d4f64155c6433
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093250B2

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