Methyl iodide → HCID 3026785, compound

HRID 1500128Notes

Reaction equation

HRID 1500128 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.[CH3:11][I:12]>ClC(Cl)C>[I-:12].[CH3:1][N+:2]([CH3:11])([CH3:10])[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 8488N,N-dimethyl-m-toluidine

Product 1

HCID 3026785HCID 3026785, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dimethyl-m-tolyl-amine (556 mg, 4.12 mmol) was dissolved in dry dichloroethane (2 mL) and methyl iodide (880 mg, 6.2 mmol) was added dropwise. The reaction was refluxed for 1 h during which time sedimentation occurred. The reaction was cooled to room temperature, the solid filtered out, washed with dichloromethane, and dried overnight in a desiccator to give a white powder (809 mg, 72% yield). 1H NMR (DMSO-d6): δ7.82 (s, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.51 (t, J=8 Hz, 1H), 7.93 J=7.5 Hz, 1H), 3.59 (s, 9H), 2.42 (s, 3H); MS (ESI, m/z): 150 (M+).

Workup

  1. temperatureThe reaction was refluxed for 1 h during which time sedimentation
  2. filtrationthe solid filtered out
  3. washwashed with dichloromethane
  4. customdried overnight in a desiccator

Sources & evidence

ORD record
ord-ff4cfd26b5234bf4a56799085478f6db
Source dataset
uspto-grants-2015_12
Patent number
US09205156B2

Reaction notes

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