Ethyl Acetate → HCID 10028030, compound

HRID 374051Notes

Reaction equation

HRID 374051 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[N:14]=[C:15]([S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=O)[NH:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.C(OCC)(=O)C.CO>O1CCCC1>[C:7]1([C:13]2[N:14]=[C:15]([S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[NH:16][C:17]=2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10413322HCID 10413322, compoundHCID 21226445Aluminium lithium hydrideHCID 21584119Ethylacetate methanol

Product 1

HCID 10028030HCID 10028030, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part B. To a solution of lithium aluminum hydride (0.96 g, 0.025 mol) in dry tetrahydrofuran (30 mL) was added, dropwise, a solution of 8-(4,5-diphenyl-1H-imidazole-2-ylthio)-N-heptyloctanamide (2.82 g, 0.0057 mol) in tetrahydrofuran (15 mL) and the reaction mixture was stirred at reflux for 18 hours. The reaction mixture was cooled to 0°, quenched by the slow and careful sequential addition of water (0.96 mL), 15% sodium hydroxide (2.88 mL), and water (2.88 mL), and then stirred at 0° for 30 minutes. The solution was then dried over magnesium sulfate and concentrated, and the residue was chromatographed with 1:1 hexane:ethyl acetate and then with a gradient of 1:0 to 3:1 to 1:1 ethyl acetate-methanol to give 8-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptyl-1-octanamine (1.07 g, 0.0022 mol) as a white solid, mp 87°-89°. 1H NMR (CDCl3) δ7.6- 7.2(m,11H), 3.1(t,2H,J=7Hz), 2.7-2.5(m,2H), 1.8-1.1(m,25H), 0.9(t,3H,J=8Hz).

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled to 0°
  3. customquenched by the slow and
  4. additioncareful sequential addition of water (0.96 mL), 15% sodium hydroxide (2.88 mL), and water (2.88 mL)
  5. dry with materialThe solution was then dried over magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was chromatographed with 1:1 hexane

Sources & evidence

ORD record
ord-1cc760ccc34e46858d596ad9f4d0e147
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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