5-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide → N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

HRID 1109050

반응식

HRID 1109050 반응식
[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][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=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>O1CCCC1>[C:7]1([C:13]2[N:14]=[C:15]([S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[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

참가 물질

4

반응물 2

HCID 28177995-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Part D. To a solution of lithium aluminum hydride, (1.52 g, 0.04 mol) in dry tetrahydrofuran (50 mL) was added, dropwise, a solution of 5-(4,5-diphenyl-1H-imidazol-2-ylthio) -N-heptylpentanamide (4.04 g, 0.009 mol) in tetrahydrofuran (25 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 (1.52 mL), 15% sodium hydroxide (4.56 mL), and water (4.56 mL), and then stirred at 0° for 30 minutes. The solution was then dried over magnesium sulfate and concentrated under vacuum, and the residue was chromatographed with a gradient of 1:0 to 3:1 to 1:1 ethyl acetate-methanol . The resulting yellow oil was triturated with cold hexane to give N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine as a white solid. A solution of this amine (0.80 g, 0.0018 mol) in ether (20 mL) was treated with a sufficient amount of ethereal HCl (about 25 mL) to cause complete precipitation of the amine as the hydrochloride salt. The reaction mixture was stirred for 15 minutes, and the supernatant liquid was decanted to afford a gummy solid, which was triturated with hot acetonitrile and then with cold hexane to give N-[5-(4,5-diphenyl-1H-imidazol- 2-ylthio)pentyl]-1-heptanamine hydrochloride (0.82 g, 0.0017 mol) as a white solid, mp 187°-190°. 1H NMR (CDCl3) δ 9.3(s,2H), 7.7-7.3(m,10H), 3.7-3.5 (m,2H), 3.0-2.7 (m,4H), 2.0-1.2(m,16H), 0.9(t,3H,J=8 Hz).

후처리

  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 (1.52 mL), 15% sodium hydroxide (4.56 mL), and water (4.56 mL)
  5. dry with materialThe solution was then dried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customthe residue was chromatographed with a gradient of 1:0 to 3:1 to 1:1 ethyl acetate-methanol
  8. customThe resulting yellow oil was triturated with cold hexane

출처 및 근거

ORD 기록
ord-35fd64a721e148a98a8b4bb7e9d4f100
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318984

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