Water → HCID 18670459, compound

HRID 1059309Notes

Reaction equation

HRID 1059309 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:23][O:24][CH2:25]Cl.O>CN(C)C=O.C(OCC)(=O)C>[CH3:23][O:24][CH2:25][N:9]1[C:8]2[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:7]=2[S:6][C:5]2[N:4]=[CH:3][CH:2]=[N:1][C:10]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 10967Bis(Chloromethyl) EtherHCID 24758Sodium hydrideHCID 18670294HCID 18670294, compound

Product 1

HCID 18670459HCID 18670459, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 ml of a solution of 7.0 g of ethyl 10H-pyrazino[2,3-b][1,4]benzothiazine-7-carboxylate in N,N-dimethylformamide was ice-cooled in a nitrogen atmosphere and 1.3 g of sodium hydride (60% oily) was added thereto. Then the resulting mixture was brought back to room temperature and stirred for 1 hour. Next, it was ice-cooled again and 2.5 ml of chloromethyl ether was dropped thereinto. After the completion of the reaction, the reaction mixture was distributed into water and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane) to thereby give 5.0 g of ethyl 10-(methoxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine-7-carboxylate as pale yellow crystals.

Workup

  1. additionwas added
  2. customwas brought back to room temperature
  3. temperaturecooled again
  4. customAfter the completion of the reaction
  5. extractionThe organic layer was extracted
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9152d7417de64d55b0c566bcf061bb12
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…