Triethylamine → HCID 14044811, compound

HRID 1449505Notes

Reaction equation

HRID 1449505 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(#N)C>[CH2:16]([S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123691-BromoheptaneHCID 145104-Aminothiophenol

Product 1

HCID 14044811HCID 14044811, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 100 ml of acetonitrile was dissolved 5.90 g of 4-aminothiophenol. To the solution were added 6.57 ml of triethylamine and 8.44 g of n-heptylbromide, followed by stirring at room temperature for 18 hours. The precipitated crystals were collected by filtration, followed by removing the solvent. To the residue was added water and the mixture was extracted with ethyl acetate. The extract was washed successively with 1N sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution and dried over anhydrous potassium carbonate. After removing the solvent, the residue was purified by silica gel column chromatography using 50 g of silica gel and using chloroform as eluent to obtain 6.06 g of the titled compound.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customby removing the solvent
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed successively with 1N sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. customAfter removing the solvent
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cd8396329b95413aae915d0d2526d1bc
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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