HCID 19607853, compound → HCID 19608139, compound

HRID 745081Notes

Reaction equation

HRID 745081 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:24]=[CH:23][C:10]([C:11]([N:13]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)=[O:5].I([O-])(=O)(=O)=[O:30].[Na+]>CO.O>[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:24]=[CH:23][C:10]([C:11]([N:13]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16](=[O:30])[CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 2

HCID 19607853HCID 19607853, compoundHCID 23667635Sodium periodate

Product 1

HCID 19608139HCID 19608139, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 4-[4-(2-methylbenzoylamino)benzoyl]-3,4-dihydro-2H-1,4-benzothiazine (0.5 g) in methanol (15 ml) is added an aqueous solution of sodium metaperiodate (0.28 g) in water (2.5 ml) and the mixture is stirred at room temperature for 72 hours. Water is added to the reaction solution and extracted with dichloromethane. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1), and recrystallized from dichloromethane/diethyl ether to give 4-[4-(2-methylbenzoylamino)benzoyl]-3,4-dihydro-2H-1,4-benzothiazin-1-oxide (0.34 g) as white powder, m.p. 240°-241° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract is dried over magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1)
  5. customrecrystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-f380eadcb0844c5098e4c9f41de53129
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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