Benzimidazole → 1-Benzyl-1H-benzimidazole

HRID 982025

반응식

HRID 982025 반응식
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[CH2:12]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 5798BenzimidazoleHCID 7498Benzyl BromideHCID 24758Sodium hydride

생성물 1

HCID 5633471-Benzyl-1H-benzimidazole수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4.96 g (42 mmol) of benzimidazole in 250 ml of tetrahydrofuran was cooled under N2 atmosphere to 0° C. and treated sequentially with 2.12 g (44 mmol) of sodium hydride (50% dispersion in oil) and 5.0 ml (42 mmol) of benzyl bromide. The resulting suspension was stirred at ambient temperature for 16 h, washed sequentially with water and saturated brine, dried over MgSO4, and concentrated. The resulting oil was taken up in 75 ml of ethyl acetate, triturated with 300 ml of hexane, and filtered. The mother liquor was concentrated and filtered, and the combined solids were dried in vacuo at 50° C. to give 7.00 g (80%) of the desired compound. 1H NMR (CDCl3) δ 5.38 (s,2H), 7.2 (m,2H), 7.3-7.4 (m,6H), 7.83 (br d,1H), 7.96 (br s,1H).

후처리

  1. washwashed sequentially with water and saturated brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customtriturated with 300 ml of hexane
  5. filtrationfiltered
  6. concentrationThe mother liquor was concentrated
  7. filtrationfiltered
  8. customthe combined solids were dried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-e0a4dd0f75e2430b9a45de23611f7082
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994477

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