Triethylamine → HCID 19041048, compound

HRID 1683799Notes

Reaction equation

HRID 1683799 reaction equation
C(N(CC)CC)C.[C:8]([Si](C)(C)C)#[N:9].[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N+:32]=3[O-])[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15]>C(#N)C>[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:8]#[N:9])[N:32]=3)[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 19041120HCID 19041120, compound

Product 1

HCID 19041048HCID 19041048, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

21.3 ml of triethylamine and 30.7 ml of cyanotrimethylsilane were added to a suspension of 26.3 g of 2-[2-(3,4-diethoxyphenyl)-4-thiazolyl]pyridine-1-oxide in 500 ml of acetonitrile. The mixture was refluxed for 62 hours. The solvent in the reaction mixture was removed by distillation. To the residue was added an aqueous sodium carbonate solution. The mixture was subjected to extraction with methylene chloride. The methylene chloride layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (elutant: methylene chloride) and recrystallized from ethanol to obtain 22.2 g of 2-(3,4-diethoxyphenyl)-4-(6-cyano-2-pyridyl)thiazole.

Workup

  1. temperatureThe mixture was refluxed for 62 hours
  2. customThe solvent in the reaction mixture was removed by distillation
  3. additionTo the residue was added an aqueous sodium carbonate solution
  4. extractionThe mixture was subjected to extraction with methylene chloride
  5. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customThe residue was purified by silica gel column chromatography (elutant: methylene chloride)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8f9e43647862435598a65a1a2abde5a4
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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