Methyl iodide → HCID 59053529, compound

HRID 1400282Notes

Reaction equation

HRID 1400282 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][N:15]([CH2:17][C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)[CH3:16].[CH3:23][I:24]>C1COCC1>[I-:24].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][N+:15]([CH2:17][C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)([CH3:23])[CH3:16]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68151500HCID 68151500, compound

Product 1

HCID 59053529HCID 59053529, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)-N-methylethanamine (38) (0.05 mmol) was dissolved in 3 mL of THF; then 0.10 mmol of MeI were added under stirring and allowed to react for 14 h at room temperature. The solvent was evaporated under vacuum and the resulting crude was triturated with 5 mL of n-hexane for 2 h. The solid was filtered and dried at 50° C. under reduce pressure to afford 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)-N,N-dimethylethanaminium iodide as a white solid (92% yield).

Workup

  1. customto react for 14 h at room temperature
  2. customThe solvent was evaporated under vacuum
  3. customthe resulting crude was triturated with 5 mL of n-hexane for 2 h
  4. filtrationThe solid was filtered
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-9585f5b7b55442e5ae2722443cef96bf
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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