Methyl iodide → HCID 13035563, compound

HRID 2059225Notes

Reaction equation

HRID 2059225 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[O:9][N:8]=1)=[O:5].[CH3:24]I>C[O-].[Na+]>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([N:6]([CH3:24])[C:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[O:9][N:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 157868Benzamide, 2,6-dichloro-N-[5-(4-chlorophenyl)-3-isoxazolyl]-

Product 1

HCID 13035563HCID 13035563, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

2,6-Dichloro-N-(5-(4-chlorophenyl)-3-isoxazolyl)benzamide (1 gram prepared according to the teaching of synthesis route III and Example 15) and sodium methoxide (160 milligrams in 100 ml. methanol) were placed in a reaction vessel and stirred for about 15 minutes. Excess methyl iodide was added and the reaction mixture was then heated to reflux for 4 hours. Upon cooling a solid formed which was filtered and then recrystallized from ethanol. NMR analysis confirmed that the final product was a mixture of exo- and endo-alkylated isoxazole, m.p.=175°-178° C.

Workup

  1. customwere placed in a reaction vessel
  2. temperaturethe reaction mixture was then heated
  3. temperatureto reflux for 4 hours
  4. temperatureUpon cooling a solid
  5. customformed which
  6. filtrationwas filtered
  7. customrecrystallized from ethanol
  8. additiona mixture of exo- and endo-alkylated isoxazole, m.p.=175°-178° C.

Sources & evidence

ORD record
ord-0f1d19e569834c7da38ee1a6cbdc7f12
Source dataset
uspto-grants-1982_03
Patent number
US04322429

Reaction notes

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