Boron trifluoride etherate → 5-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide

HRID 374046

반응식

HRID 374046 반응식
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([NH2:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:33][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:25])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 81271-HeptanamineHCID 189587125-[(4,5-Diphenyl-1H-imidazol-2-YL)sulfanyl]pentanoic acid

생성물 1

HCID 28177995-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide수율 87.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Part C, Method 2. To a solution of 5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid (2.0 g, 0.0057 mol) in toluene (35 mL) was added heptylamine (1.63 mL, 1.27 g, 0.011 mol) and then boron trifluoride etherate (1.35 mL, 1.56 g, 0.011 mol) and the reaction mixture was stirred at reflux for 120 hours using a Dean-Stark moisture trap. The reaction mixture was cooled, extracted with 0.1N NaOH, 0.1N HCl, and water, and the combined organic extracts were dried over magnesium sulfate and concentrated under vacuum. The residue was chromatographed and worked-up as described in Part C, Method 1, to give 5-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide (2.35 g, 0.005 mol) as a white solid.

후처리

  1. temperatureat reflux for 120 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with 0.1N NaOH, 0.1N HCl, and water
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-7799a0f58e784e34b49bfbaa66a0ae8d
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166214

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