Methyl iodide → HCID 19921676, compound

HRID 1647786Notes

Reaction equation

HRID 1647786 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][N:13]([CH3:15])[CH3:14])#[N:2].[CH3:16][I:17]>C1COCC1>[I-:17].[CH3:14][N+:13]([CH3:16])([CH3:15])[CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 330335-Cyanogramine

Product 1

HCID 19921676HCID 19921676, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.7 g (13.6 mmol, 1.0 equiv.) of 5-cyano-3-(dimethylamino)methyl-1H-indole in 125 mL of THF at 0° C. was added 1.3 mL (20.3 mmol, 1.5 equiv.) of methyl iodide dropwise. After five minutes the solution was allowed to warm to room temperature and stirred for one hour. The resulting precipitate was filtered and dried in vacuo to yield 4.4 g (96%) of N,N,N-trimethyl-1-(5-cyano-1H-indol-3-yl)methanaminium iodide, pure by 1H NMR analysis.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-c146cf92b90048c98395a6c5c59099f9
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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