Dimethyl Sulfoxide → (1-benzyl-1H-imidazol-2-yl)acetonitrile

HRID 1253031

반응식

HRID 1253031 반응식
[C-:1]#[N:2].[Na+].CS(C)=O.Cl.[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH2:9]([N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][C:1]#[N:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 27792431-benzyl-2-(chloromethyl)-1H-imidazole hydrochloride

생성물 1

HCID 817477(1-benzyl-1H-imidazol-2-yl)acetonitrile수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

Dry, powdered sodium cyanide (14 gm, 280 mmole) was added to 80 ml of dry dimethylsulfoxide with stirring at 23° C. Then 1-benzyl-2-chloromethylimidazole hydrochloride (14 gm, 63 mmole) was added portionwise over 10 minutes while maintaining the temperature below 40° C. After the addition was complete, the mixture was stirred at 40° C. for an additional hour. It was diluted with 250 ml methylene chloride and the resulting solution was washed with 4×200 ml of water, dried over MgSO4 and the solvent removed in vacuo. The residue was collected by filtration, dissolved in warm methanol and precipitated with ether to obtain needle-like crystals (8.7 g) of N-benzyl-2-cyanomethylimidazole. m.p. 102.5°-104° C.

후처리

  1. customDry
  2. temperaturewhile maintaining the temperature below 40° C
  3. additionAfter the addition
  4. stirringthe mixture was stirred at 40° C. for an additional hour
  5. washthe resulting solution was washed with 4×200 ml of water
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo
  8. filtrationThe residue was collected by filtration
  9. dissolutiondissolved in warm methanol
  10. customprecipitated with ether

출처 및 근거

ORD 기록
ord-0b1e89ca57df41b2b83c32e76e0a5fab
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04746669

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