Methyl iodide → HCID 19101549, compound

HRID 1974474Notes

Reaction equation

HRID 1974474 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH:17]3[C:22](=[O:23])[NH:21][C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[S:18]3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:30]I>CN(C)C=O>[CH3:30][N:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][CH:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:10]2[CH2:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)[C:22]1=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15027925HCID 15027925, compound

Product 1

HCID 19101549HCID 19101549, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.77 g (=0.004 m) of 2-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-butyl]-2H-1,4-benzothiazine-3(4H)one (see Example 10) prepared analogously to Example were dissolved in 20 ml of anhydrous dimethylformamide with stirring. 0.121 g of sodium hydride was added under a nitrogen atmosphere, and the resulting suspension was maintained at room temperature for 10 minutes. 0.70 g of methyl iodide was then added all at once, and the reaction mixture was stirred for 2.5 hours at room temperature. The reaction mixture was worked up by distilling off the solvent, adding 100 ml of water to the residue, and extracting the mixture with 100 ml of ethyl acetate. The organic phase was concentrated by evaporating the solvent, and the crude title compound which remained as a residue was purified by column chromatography. 0.6 g of 4-methyl-2-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-butyl]-2H-1,4-benzothiazine-3(4H)-one was obtained as beige-colored powder.

Workup

  1. stirringwas stirred for 2.5 hours at room temperature
  2. distillationby distilling off the solvent
  3. additionadding 100 ml of water to the residue
  4. extractionextracting the mixture with 100 ml of ethyl acetate
  5. concentrationThe organic phase was concentrated
  6. customby evaporating the solvent
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5cbfee57f03e44f1837a15f6f08a1406
Source dataset
uspto-grants-1994_02
Patent number
US05283243

Reaction notes

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