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

HRID 1109050

反応式

HRID 1109050 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-35fd64a721e148a98a8b4bb7e9d4f100
出典データセット
uspto-grants-1994_06
特許番号
US05318984

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