Methyl iodide → HCID 54508469, compound

HRID 36894Notes

Reaction equation

HRID 36894 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([S-:20])=[S:19])[CH2:14][CH2:13]1.[Na+].[CH3:22]I>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([S:20][CH3:22])=[S:19])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 23695420sodium 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carbodithioate

Product 1

HCID 54508469HCID 54508469, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carbodithioate (3 g, prepared in the previous Example) and methyl iodide (0.5 ml) in 95% ethanol (15 ml) is refluxed for one hour. The orange reaction mixture is concentrated, taken up with ether and washed with water. The organic phase is dried over sodium sulfate and concentrated. After chromatography on silica gel (eluent: cyclohexane/AcOEt 70/30), methyl 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carbodithioate (13 g) is obtained in the form of an oil, which is taken up with pentene to give a white solid.

Workup

  1. temperatureis refluxed for one hour
  2. concentrationThe orange reaction mixture is concentrated
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a8537d9c43449d3a739c166cafcbc0e
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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