Sodium Cyanide → 4-Cyanomethyl-2-(p-methoxyphenyl)-5-methyl-imidazole

HRID 839127ノート

反応式

HRID 839127 の反応式
Cl.O[CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[NH:7][C:8]=1[CH3:9].S(=Cl)=O.[C-:21]#[N:22].[Na+]>C(Cl)(Cl)Cl.CS(C)=O>[C:21]([CH2:3][C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[NH:7][C:8]=1[CH3:9])#[N:22]

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 203258964-Hydroxymethyl-2-p-methoxyphenyl-5-methyl-imidazole hydrochlorideHCID 57465351CID 57465351

生成物 1

HCID 203258944-Cyanomethyl-2-(p-methoxyphenyl)-5-methyl-imidazole収率 91%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6212Chloroform溶媒2 回

実験手順

To a stirred slurry of 15.3 g (0.06 mole) of 4-hydroxymethyl-2-p-methoxyphenyl-5-methyl-imidazole hydrochloride in 200 ml of chloroform are added 15 g (0.12 mole) of thionyl chlorine in CHCl3. Vigorous evolution of gas is observed during the addition. The reaction mixture is stirred at room temperature for 5 hours, during which time the slurry dissolves to form a pale pink solution. The solvent is then removed under reduced pressure and the solid residue taken up in fresh CHCl3. The solution is then filtered, ether is added until cloudy and then chilled. White crystals of 5-chloromethyl-2-p-methoxyphenyl-4-methyl-imidazole hydrochloride are precipitated, filtered and collected (91% yield), m.p. 203°-205° C (dec.). This chloromethyl derivative is dissolved in 75 ml of warm DMSO and added to a hot solution of 15 g (0.3 mole) of sodium cyanide in DMSO. The reaction mixture is stirred at room temperature for 16 hours and warmed to 60° C for 4 hours, then allowed to cool to room temperature and poured over 1 liter of ice and stirred. A yellow solid is precipitated, filtered and air-dried. Three recrystallizations from methylene chloride-hexane give the product, 4-cyanomethyl-2-(p-methoxyphenyl)-5-methyl-imidazole, as fluffy white crystals, m.p, 158°-160° C.

後処理

  1. additionVigorous evolution of gas is observed during the addition
  2. dissolutiondissolves
  3. customto form a pale pink solution
  4. customThe solvent is then removed under reduced pressure
  5. filtrationThe solution is then filtered
  6. additionether is added until cloudy
  7. temperaturechilled
  8. customWhite crystals of 5-chloromethyl-2-p-methoxyphenyl-4-methyl-imidazole hydrochloride are precipitated
  9. filtrationfiltered
  10. customcollected (91% yield), m.p. 203°-205° C (dec.)
  11. dissolutionThis chloromethyl derivative is dissolved in 75 ml of warm DMSO
  12. stirringThe reaction mixture is stirred at room temperature for 16 hours
  13. temperaturewarmed to 60° C for 4 hours
  14. temperatureto cool to room temperature
  15. stirringstirred
  16. customA yellow solid is precipitated
  17. filtrationfiltered
  18. customair-dried
  19. customThree recrystallizations from methylene chloride-hexane

出典と根拠

ORDレコード
ord-8ff9cd2b9e6f4a3484862f031f46cecc
出典データセット
uspto-grants-1978_06
特許番号
US04093811

反応ノート

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