Sulfuric Acid → HCID 89876280, compound

HRID 1487084Notes

Reaction equation

HRID 1487084 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:10]([C:13]2[CH:14]=[CH:15][C:16]([C:23]#[C:24][Si](C)(C)C)=[C:17]([CH:22]=2)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11])=[CH:5][CH:4]=1)[CH3:2].[OH:33]S(O)(=O)=O>CC(C)=O>[C:23]([C:16]1[CH:15]=[CH:14][C:13]([S:10](=[O:11])(=[O:12])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH2:29][CH:30]([CH3:31])[CH3:32])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:33])[CH3:24]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 89875948HCID 89875948, compound

Product 1

HCID 89876280HCID 89876280, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-((trimethylsilyl)ethynyl)benzoate (320 mg, 0.678 mmol), mercuric sulphate (201 mg, 0.678 mmol), H2SO4 (1.357 mL, 1.357 mmol) and acetone (6 mL) was heated at reflux for 4 hours. The mixture was partitioned between ammonium chloride solution (10%, 20 mL) and dichloromethane (DCM) (2×25 mL) then organics separated, dried (MgSO4) and evaporated onto florisil. The crude material was purified by silica (Si) chromatography (0-100% dichloromethane-cyclohexane gradient) to give the title compound as a colourless gum, 110 mg. LCMS [LCMS1] Rt 1.33 min, m/z (ES+) 418 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe mixture was partitioned between ammonium chloride solution (10%, 20 mL) and dichloromethane (DCM) (2×25 mL)
  4. dry with materialorganics separated, dried (MgSO4)
  5. customevaporated onto florisil
  6. customThe crude material was purified by silica (Si) chromatography (0-100% dichloromethane-cyclohexane gradient)

Sources & evidence

ORD record
ord-aa44235e36e04dd98835bc529f9f00a6
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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