HCID 19607853, compound → HCID 19608139, compound

HRID 1291643Notes

Reaction equation

HRID 1291643 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-06531f3b509d44eb84f3f75d084fc88c
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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