Methyl iodide → HCID 18372248, compound

HRID 2301266Notes

Reaction equation

HRID 2301266 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:18])[S:5]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=1[CH3:17])(=[O:7])=[O:6].[CH3:19]I>CN(C)C=O>[CH3:18][N:4]([CH3:3])[S:5]([C:8]1[S:12][C:11]([N:13]([CH3:19])[C:14](=[O:16])[CH3:15])=[N:10][C:9]=1[CH3:17])(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18372250HCID 18372250, compound

Product 1

HCID 18372248HCID 18372248, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.0 g of sodium hydride (60% dispersion in mineral oil, 0.151 mol) were added dropwise at 0° C. to a solution of 36.2 g (0.137 mol) of N-{5-[(dimethylamino)-sulphonyl]-4-methyl-1,3-thiazol-2-yl}acetamide in dimethylformamide. Then 21.4 g (0.151 mol) of methyl iodide were added dropwise from a syringe. After TLC showed complete conversion, the mixture was quenched by adding a saturated ammonium chloride solution. The mixture was evaporated to dryness, and the residue was taken up with water, stirred for 16 h and filtered off. After the residue had been dried in vacuo it was further purified by chromotography on silica gel with toluene/ethyl acetate (15-66% ethyl acetate) as mobile phase. 31.0 g of a white powder were obtained (Rf=0.43 (toluene/ethyl acetate=1/2), yield 74%).

Workup

  1. customthe mixture was quenched
  2. additionby adding a saturated ammonium chloride solution
  3. customThe mixture was evaporated to dryness
  4. filtrationfiltered off
  5. customAfter the residue had been dried in vacuo it
  6. customwas further purified by chromotography on silica gel with toluene/ethyl acetate (15-66% ethyl acetate) as mobile phase

Sources & evidence

ORD record
ord-6d769b0d42774bc4a4036ec5038ac430
Source dataset
uspto-grants-2002_12
Patent number
US06500817B1

Reaction notes

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