Ethanol → HCID 18670209, compound

HRID 1059424Notes

Reaction equation

HRID 1059424 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][N:16]4C(=O)C5=CC=CC=C5C4=O)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.C(O)C>O.NN>[NH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:7]2[S:6][C:5]3[N:4]=[CH:3][CH:2]=[N:1][C:10]=3[NH:9][C:8]=2[CH:11]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 18670092HCID 18670092, compound

Product 1

HCID 18670209HCID 18670209, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Conditions

Temperature
80 °C

Procedure

7.9 g of N-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimide was suspended in hydrazine monohydrate (10 ml)/ethanol (50 ml) and the reaction mixture was heated to 80° C. for 20 minutes. Then the reaction mixture was brought back to room temperature. After distilling off the solvent under reduced pressure, the residue was distributed into an aqueous solution of potassium carbonate and ethyl acetate. The organic layer was extracted and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue thus obtained was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia) to thereby give 5.0 g of the title compound as yellow orthorhombic crystals.

Workup

  1. customwas brought back to room temperature
  2. distillationAfter distilling off the solvent under reduced pressure
  3. extractionThe organic layer was extracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record
ord-0df30f1ee1a3499e9f30e7eedbfe5de2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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