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

HRID 374046

Reaction equation

HRID 374046 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7799a0f58e784e34b49bfbaa66a0ae8d
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Linked notes

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