Triethylamine → HCID 20093314, compound

HRID 274675Notes

Reaction equation

HRID 274675 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:14]=NC=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:21](CC)CC)C.[F:26][C:27](F)(F)[C:28]([O:30]C(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:21]=[CH:19][CH:14]=1)[C:28](=[O:30])[CH2:27][F:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86748461HCID 86748461, compound

Product 1

HCID 20093314HCID 20093314, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.27 g (28.1 mmol) 4-[3-(N-benzylaminopropylthio)pyridine and 4.70 ml (33.7 mmol) of triethylamine in 150 ml of methylene chloride, 4.76 ml (33.7 mmol) of trifluoroacetic anhydride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=2:1 to 1:1) to obtain 6.04 g of 4-[3-(N-benzyl-N-fluoroacetylamino)-propylthio]pyridine (yield: 60.7% yellow oil).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate/hexane=2:1 to 1:1)

Sources & evidence

ORD record
ord-f9d12759410c46e483a652ad99056f62
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

Loading…