Ethyl Acetate → 10H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetonitrile

HRID 1059362Notes

Reaction equation

HRID 1059362 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[NH:8][C:7]=2[CH:16]=1.[C-:17]#[N:18].[Na+].C(OCC)(=O)C>CS(C)=O>[N:15]1[C:9]2[NH:8][C:7]3[CH:16]=[C:3]([CH2:2][C:17]#[N:18])[CH:4]=[CH:5][C:6]=3[S:11][C:10]=2[N:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 117470388-Chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 1867021210H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetonitrileYield 104.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 50 ml of a solution of 5 g of 8-(chloromethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine in dimethyl sulfoxide was added 0.92 g of sodium cyanide and the resulting mixture was reacted at 60° C. for 1 hour. After adding ethyl acetate, the organic layer was washed with water and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 4.7 g of the title compound was obtained as a yellow solid.

Workup

  1. customthe resulting mixture was reacted at 60° C. for 1 hour
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-02f8a7f907f347bdb1184a2b5f6fe089
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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