Imidazole → 4-(Imidazol-1-ylmethyl)benzonitrile

HRID 1421775노트

반응식

HRID 1421775 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1>CN(C=O)C>[N:1]1([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrile

생성물 1

HCID 12364494-(Imidazol-1-ylmethyl)benzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To imidazole (7 gm, 103 mmol) suspended in degassed DMF (250 mL) under argon was added NaH 60% dispersion in mineral oil (4.53 gm, 113 mmol) with stirring for 10 minutes. A solution of 4-bromomethyl benzonitrile in 50 mL of DMF was added and the reaction was stirred for 16 hrs. The reaction was quenched with the addition of 20 mL of water and the solvent was removed in vacuo. The residue was suspended in methylene chloride (500 mL) and extracted 3 times with water (200 mL) and the organic layer was dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. The residue was chromatographed on silica gel with methylene chloride to remove the oil followed by 95:5 methylene chloride: methanol. The resulting fractions where reduced to a small volume in vacuo and the product spontaneously crystallized. The crystals were filtered to give the desired product.

후처리

  1. stirringthe reaction was stirred for 16 hrs
  2. customThe reaction was quenched with the addition of 20 mL of water
  3. customthe solvent was removed in vacuo
  4. extractionextracted 3 times with water (200 mL)
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel with methylene chloride
  9. customto remove the oil
  10. customthe product spontaneously crystallized
  11. filtrationThe crystals were filtered

출처 및 근거

ORD 기록
ord-a5cd0ba121f649cf820a17135b664a0e
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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