Hydrochloric Acid → 2-(3,5-Di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-4-sulfomethyl-2H-1,4-benzothiazine

HRID 1078211Notes

Reaction equation

HRID 1078211 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[CH:10]=[C:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)([CH3:6])([CH3:5])[CH3:4].Cl[CH2:31][S:32]([O-:35])(=[O:34])=[O:33].[K+].Cl>CC(C)=O>[C:3]([C:7]1[CH:8]=[C:9]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[CH:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:31][S:32]([OH:35])(=[O:34])=[O:33])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 53806442HCID 53806442, compoundHCID 86749733Potassium (chloro)methanesulfonate

Product 1

HCID 570864732-(3,5-Di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-4-sulfomethyl-2H-1,4-benzothiazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a suspension of sodium hydride (60% suspension in paraffin liquid, 0.042 g) in dimethylformaldehyde (1 ml), 2-(3, 5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (0.20 g) dissolved in dimethylformalhyde (2 ml) was added, dropwise, under ice-cooling and a nitrogen atmosphere. The mixture was stirred for 40 minutes at room temperature. To the mixture, potassium (chloro)methanesulfonate (0,096 g) dissolved in dimethylformaldehyde (2 ml) was added, dropwise, and the mixture was stirred for one day at room temperature. 1N hydrochloric acid was added to the mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give the titled compound.

Workup

  1. dissolutiondissolved in dimethylformalhyde (2 ml)
  2. additionwas added
  3. temperaturedropwise, under ice-cooling
  4. additionwas added
  5. stirringdropwise, and the mixture was stirred for one day at room temperature
  6. extractionthe whole was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8e6da023a783438181563b276b29f96a
Source dataset
uspto-grants-1996_08
Patent number
US05547952

Reaction notes

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