Methyl iodide → HCID 17798127, compound

HRID 1016324Notes

Reaction equation

HRID 1016324 reaction equation
[H-].[Na+].C1COCC1.[Br:8][C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13]4=[C:14]([C:25](=[O:35])[C:26]([CH2:28]C5C=NC=CC=5)=[CH:27][N:12]4[C:11]=2[CH:10]=1)[CH:15]=[C:16]([O:23][CH3:24])[CH:17]=3.CI>CS(C)=O.O>[Br:8][C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13]4=[C:14]([C:25](=[O:35])[C:26]([CH3:28])=[CH:27][N:12]4[C:11]=2[CH:10]=1)[CH:15]=[C:16]([O:23][CH3:24])[CH:17]=3

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 12021104HCID 12021104, compound

Product 1

HCID 17798127HCID 17798127, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium hydride(840 mg) in DMSO(200 mL) was stirred at 60-70° C. for 30 min. After addition of THF (60 mL), the mixture was cooled down to 0° C. To the mixture were added dropwise a solution in DMSO of the compound (7g) obtained in Example 36 <step 2>, then methyl iodide (1.33 mL). After stirring for 1 hour, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was suspended in dioxane (5 mL) and to the suspension was added DDQ (1.22 g). The mixture was heated under reflux for 3 hours. After allowing the reaction mixture to cool to room temperature, IN sodium hydroxide (20 mL) and ethyl acetate (50 mL) were added. The precipitated crystals were collected by filtration and washed with water and ethanol. The resultant compound (1.1 g) was suspended in dioxane (60 mL) and to the suspension was added DDQ (1.2 g). The mixture was heated under reflux for 3 hours. After allowing the reaction mixture to cool to room temperature, to the mixture were added 1N-sodium hydroxide (20 mL) and ethyl acetate(50 mL). The precipitated crystals were collected by filtration and washed with water and ethanol to obtain the title compound (1.1 g; 11%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionwas added DDQ (1.22 g)
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. temperatureto cool to room temperature, IN sodium hydroxide (20 mL)
  9. additionethyl acetate (50 mL) were added
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with water and ethanol
  12. additionwas added DDQ (1.2 g)
  13. temperatureThe mixture was heated
  14. temperatureunder reflux for 3 hours
  15. temperatureto cool to room temperature, to the mixture
  16. additionwere added 1N-sodium hydroxide (20 mL) and ethyl acetate(50 mL)
  17. filtrationThe precipitated crystals were collected by filtration
  18. washwashed with water and ethanol

Sources & evidence

ORD record
ord-e41b146d5138445c9cfa18932146a693
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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