Methyl iodide → HCID 19786578, compound

HRID 1646719Notes

Reaction equation

HRID 1646719 reaction equation
CN([CH2:4][CH:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1)C.CI.[I-]>CO>[CH2:4]=[C:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 30165Iodide IonHCID 19786540HCID 19786540, compound

Product 1

HCID 19786578HCID 19786578, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6,7-Dihydro-5-dimethylaminomethyl-3-phenyl-1,2-benzisoxazole-4(5H)-one free base (3.0 g) was dissolved in 3 ml of methanol and added in one portion to 5 ml (excess) of methyl iodide. As the quaternary iodide began to separate, additional methanol was added to facilitate stirring. After stirring overnight the reaction mixture was poured into 5% sodium bicarbonate solution and extracted with ether. The organic phase was washed with 5% HCl and then dried, evaporated, and recrystallized from hexane to give 2.05 g of 6,7-dihydro-5-methylene-3-phenyl-1,2-benzisoxazol-4(5H)-one, m.p. 97°-99° C.

Workup

  1. customto separate
  2. additionadditional methanol was added
  3. stirringAfter stirring overnight the reaction mixture
  4. additionwas poured into 5% sodium bicarbonate solution
  5. extractionextracted with ether
  6. washThe organic phase was washed with 5% HCl
  7. customdried
  8. customevaporated
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e86ebbc601b046d3a3d77dc8a7ce1e8b
Source dataset
uspto-grants-1993_01
Patent number
US05180834

Reaction notes

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