Ethyl Acetate → HCID 14988446, compound

HRID 1198481Notes

Reaction equation

HRID 1198481 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[C:6]2[C:11]=1[S:10](=O)[CH2:9][CH2:8][NH:7]2.C(OCC)(=O)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][NH:7]2

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 14988455HCID 14988455, compound

Product 1

HCID 14988446HCID 14988446, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-chloro-3,4-dihydro-2H-1,4-benzothiazine-5-carboxylic acid-1-oxide (2.5 g) and stannous chloride dihydrate (4.51 g) in methanol (20 ml) was refluxed for 21 hours. To the reaction mixture was added ethyl acetate (200 ml), washed with water and dried over anhydrous sodium sulfate. After concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography eluting with dichloromethane-ethanol (9:1) to give the title compound (450 mg, 19.6%). This compound was recrystallized from ethanol to give yellow needles, mp 220° C.

Workup

  1. temperaturewas refluxed for 21 hours
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography
  6. washeluting with dichloromethane-ethanol (9:1)

Sources & evidence

ORD record
ord-989a0e61f7dd456491b195740e3faab1
Source dataset
uspto-grants-1994_01
Patent number
US05281600

Reaction notes

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