Sodium Carbonate → HCID 23365818, compound

HRID 1080693Notes

Reaction equation

HRID 1080693 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1I.[CH3:15][Si:16]([C:19]#[C:20][Si](C)(C)C)([CH3:18])[CH3:17].C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:13][NH:12][S:9]([CH2:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:19]([Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:20]2)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 84564Bis(trimethylsilyl)acetyleneHCID 107584621-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamide

Product 1

HCID 23365818HCID 23365818, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Amino-3-iodo-N-methyl-benzenemethanesulfonamide (1.63 g, 0.005 mol), bis(trimethylsilyl)acetylene (1.28 g, 0.0075 mol) and tetrakistriphenylphosphine Pd(O) (0.578 g, 0.0005 mol) were dissolved in DME (50 mL) and followed by the addition of saturated aqueous Na2CO3 (5 mL). The mixture was heated at reflux for 48 h. The solvent was removed in vacuo. The residue was dissolved in EtOAc and extracted with brine. The organic layer was dried over Na2SO4, filtered and evaporated in vacuo. Silica gel chromatography (10-100% EtOAc gradient in hexane) of the residue afforded the product (4) (1.08 g, 76.8%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. extractionextracted with brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-98010caf42f740ae81bde8e6740038cb
Source dataset
uspto-grants-1996_12
Patent number
US05583149

Reaction notes

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