Methyl iodide → Methyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65072노트

반응식

HRID 65072 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[NH:4]1.[C:17](=[S:19])=[S:18].[CH2:20](N(CC)CC)C.CI>CS(C)=O>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[N:4]1[C:17]([S:19][CH3:20])=[S:18]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

생성물 1

HCID 13375530Methyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate수율 90%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

(1RS, 3RS)-cis-3-Hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (4.326 g) is dissolved in dimethylsulfoxide (20 ml), and thereto are added CS2 (2.4 ml) and triethylamine (5.6 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise methyl iodide (2.5 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, 5% HCl and water in order, dried over sodium sulfate and then distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (5.5 g, 90%) as colorless needles, m.p. 164°-166° C., NMR (CDCl3, δ): 1.68 (d, J=6.8 Hz, 3H, C1 --CH3), 2.73 (s, 3H, CSSCH3); Mass m/e: 306 (M+), 258 (M+ --CH 3 SH).

후처리

  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% HCl and water in order
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is recrystallized from aqueous ethanol

출처 및 근거

ORD 기록
ord-332c494c01eb42aa973a21aa6f49dcd1
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04612317

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