Iodoethane → Ethyl (1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65077ノート

反応式

HRID 65077 の反応式
[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[NH:4]1)[CH3:2].[C:18](=[S:20])=[S:19].[CH2:21](N(CC)CC)[CH3:22].C(I)C>CS(C)=O>[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[N:4]1[C:18]([S:20][CH2:21][CH3:22])=[S:19])[CH3:2]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741006(1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

生成物 1

HCID 86741017Ethyl (1RS, 3SR)-trans-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate収率 71%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

(1RS, 3SR)-trans-1-Ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (0.461 g) is dissolved in dimethylsulfoxide (2 ml), and thereto are added CS2 (0.27 ml) and triethylamine (0.61 ml). The mixture is stirred at room temperature for one hour, and thereto is added dropwise ethyl iodide (0.38 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured onto ice-water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate and then distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (0.477 g, 71%) as colorless needles, m.p. 82°-84° C., NMR (CDCl3, δ): 1.40 (t, J=7.0 Hz, 3H, CSSCH2CH3); Mass m/e: 334 (M+), 272 (M+ --CH3CH2SH).

後処理

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is recrystallized from aqueous ethanol

出典と根拠

ORDレコード
ord-abb64ae05e0b47a79a5cdf6d6a9f60d8
出典データセット
uspto-grants-1986_09
特許番号
US04612317

反応ノート

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