Methyl iodide → HCID 19921676, compound

HRID 1463334Notes

Reaction equation

HRID 1463334 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-eedc7341dc364327a59351f740e0144d
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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