Triethylamine → HCID 21709029, compound

HRID 651579Notes

Reaction equation

HRID 651579 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:12]([OH:14])=O)[CH2:3]1.S(Cl)(Cl)=O.[CH2:19]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C1C=CC=CC=1.ClCCl>[CH2:26]([N:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12]([CH:4]1[CH2:3][C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5]1)=[O:14])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8920DihexylamineHCID 24386Thionyl ChlorideHCID 11839188HCID 11839188, compound

Product 1

HCID 21709029HCID 21709029, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20.00 g of (4-oxo-thiochroman-2-yl)-carboxylic acid in 200 ml of benzene was added 14.0 ml of thionyl chloride, followed by reflux under heating for 3 hours. The reaction solution was concentrated under reduced pressure to give a residue, a solution of which in 100 ml of dichloromethane was added dropwise to a solution of 24.6 ml of dihexylamine and 20.0 ml of triethylamine in 200 ml of dichloromethane under ice-cooling with stirring. After stirring at room temperature overnight, the reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate, and the mixture was washed with water, 1 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=5:1-3:1) and recrystallized from hexane to give 29.22 g of N,N-dihexyl-(4-oxo-thiochroman-2-yl)-carboxamide.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 3 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customto give a residue
  5. temperaturecooling
  6. stirringAfter stirring at room temperature overnight
  7. concentrationthe reaction solution was concentrated under reduced pressure
  8. additionto the residue was added ethyl acetate
  9. washthe mixture was washed with water, 1 N hydrochloric acid
  10. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  11. customAfter removal of the drying agent
  12. filtrationby filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=5:1-3:1)
  15. customrecrystallized from hexane

Sources & evidence

ORD record
ord-cd9c55a463ee4973b3b35391c2ea7e46
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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