Methyl iodide → HCID 70051873, compound

HRID 266479Notes

Reaction equation

HRID 266479 reaction equation
[CH:1]([Li])(CC)C.[CH2:6]([C:8]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[C:15]2[C:9]=1[C:10](=[O:23])[NH:11][S:12]2(=[O:14])=[O:13])[CH3:7].CI>O1CCCC1>[CH2:6]([C:8]1[C:18]([O:19][CH3:20])=[C:17]([CH3:1])[C:16]([O:21][CH3:22])=[C:15]2[C:9]=1[C:10](=[O:23])[NH:11][S:12]2(=[O:13])=[O:14])[CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14984048HCID 14984048, compoundHCID 178418400CID 53628100

Product 1

HCID 70051873HCID 70051873, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

s-Butyllithium (0.87M in cyclohexane, 20.4 mL) was added dropwise during one hour with stirring at -78° C. to a solution of 4-ethyl-5,7-dimethoxysaccharin (Example 22L, 2.2 g) in tetrahydrofuran (100 mL). After continued stirring at -78° C. for one hour methyl iodide (1.5 mL) was added. Stirring was continued at -78° C. for 15 minutes, the temperature was allowed to rise to room temperature, and the mixture was quenched in water. Aqueous sodium hydroxide (0.5%, 200 mL) was added. The mixture was washed with ethyl acetate (200 mL), acidified with concentrated hydrochloric acid and extracted with ethyl acetate (200 mL). The ethyl acetate extract was washed with aqueous sodium thiosulfate (10%, 50 mL) and saturated aqueous sodium chloride (50 mL), dried over sodium sulfate and stripped of ethyl acetate affording 4-ethyl-5,7-dimethoxy-6-methylsaccharin (0.73 g, 32% yield).

Workup

  1. additionwas added
  2. customto rise to room temperature
  3. customthe mixture was quenched in water
  4. additionAqueous sodium hydroxide (0.5%, 200 mL) was added
  5. washThe mixture was washed with ethyl acetate (200 mL)
  6. extractionextracted with ethyl acetate (200 mL)
  7. extractionThe ethyl acetate extract
  8. washwas washed with aqueous sodium thiosulfate (10%, 50 mL) and saturated aqueous sodium chloride (50 mL)
  9. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-25b57f4dfb75478796416420b1d1cc29
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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