Methyl iodide → 2-[4-(5-Carbamoyloxymethyl-isoxazol-3-yl)-phenoxymethyl]-1-methyl-pyridinium iodide

HRID 72336Notes

Reaction equation

HRID 72336 reaction equation
[I:1][CH3:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:21]=[C:20]([CH2:22][O:23][C:24](=[O:26])[NH2:25])[O:19][N:18]=2)=[CH:13][CH:12]=1>>[I-:1].[C:24]([O:23][CH2:22][C:20]1[O:19][N:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N+:3]=3[CH3:2])=[CH:16][CH:15]=2)[CH:21]=1)(=[O:26])[NH2:25]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 46893377Carbamic acid 3-[4-(pyridin-2-ylmethoxy)-phenyl]-isoxazol-5-ylmethyl ester

Product 1

HCID 666175602-[4-(5-Carbamoyloxymethyl-isoxazol-3-yl)-phenoxymethyl]-1-methyl-pyridinium iodide

Conditions

Temperature
80 °C

Procedure

2 ml of iodomethane was added to 0.3 g of the compound carbamic acid 3-[4-(pyridin-2-ylmethoxy)-phenyl]-isoxazol-5-ylmethyl ester in Example 65 and stirred at 80° C. for 10 hours. A crude solid compound obtained after distillation of the solution under reduced pressure to remove an excess of MeI was recrystallized from ethyl acetate/hexane/methylene chloride to obtain 2-[4-(5-carbamoyloxymethyl-isoxazol-3-yl)-phenoxymethyl]-1-methyl-pyridinium iodide as a desired compound.

Workup

  1. customA crude solid compound obtained
  2. distillationafter distillation of the solution under reduced pressure
  3. customto remove an excess of MeI
  4. customwas recrystallized from ethyl acetate/hexane/methylene chloride

Sources & evidence

ORD record
ord-e34c5829394a4b9ea6b994b276744f62
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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