N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamide → HCID 19021759, compound

HRID 374053Notes

Reaction equation

HRID 374053 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]1[NH:22][C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:25]=1)[CH2:8][CH2:9][CH3:10]>O1CCCC1>[CH2:7]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]1[NH:25][C:24]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:22]=1)[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 19021729N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 19021759HCID 19021759, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Part B. To a solution of lithium aluminum hydride (0.46 g, 0.012 mol) in dry tetrahydrofuran (15 mL) was added, dropwise, a solution of N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamide (1.20 g, 0.0027 mol) in tetrahydrofuran (8 mL) and the reaction mixture was stirred at reflux for 18 hours. The reaction mixture was cooled to 0° C. and quenched by the slow and careful sequential addition of water (0.46 mL), 15% sodium hydroxide (1.38 mL), and water (1.38 mL) and then the reaction mixture was stirred at 0° for 30 minutes. The solution was dried over magnesium sulfate and concentrated under vacuum, and the residue was chromatographed with 1:1 hexane-ethyl acetate and then with a gradient of 1:0 to 8:2 to 1:1 ethyl acetate-methanol. The resulting solid was triturated with hexane to give N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamine (0.45 g, 0.001 mol) as a white solid, mp 75°-78°. 1H NMR (CDCl3) δ7.6-7.1(m,10H), 3.1(t,2H,J=7Hz), 2.5(t,2H,J=7Hz), 1.7-1.0(m,16H), 0.9(t,3H,J=8Hz).

Workup

  1. temperatureat reflux for 18 hours
  2. customquenched by the slow and
  3. additioncareful sequential addition of water (0.46 mL), 15% sodium hydroxide (1.38 mL), and water (1.38 mL)
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customthe residue was chromatographed with 1:1 hexane-ethyl acetate
  7. customThe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-0e9ec488212c4057a0984aa52bf9e870
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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