Methyl iodide → HCID 18932266, compound

HRID 1597793Notes

Reaction equation

HRID 1597793 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1.[CH3:24]I.[Cl-].[NH4+]>CN(C)C=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:24])[C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7642407HCID 7642407, compound

Product 1

HCID 18932266HCID 18932266, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.1 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 102.0 mg of N-(benzothiazol-2-ylmethoxy)acetamide (prepared as described in Example 1) in 2 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred for 5 minutes, after which 0.023 ml of methyl iodide were added, the temperature of the resulting mixture was elevated to room temperature and the mixture was then stirred for 1.5 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate to give 106.8 mg (yield 100%) of the title compound as a solid having a melting point of 119° to 120° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was then stirred for 1.5 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed consecutively with water
  7. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through silica gel using a 1:1
  10. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-d23fb7ef049c49aead4988e2f72691dd
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

Loading…