Triethylamine → HCID 15007772, compound

HRID 847368Notes

Reaction equation

HRID 847368 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:7][CH:6]=1)[CH2:3][OH:4].C(N(CC)CC)C.[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:30]=1[C:31](Cl)=O.S(Cl)(Cl)=O>O1CCCC1.C1C=CC=CC=1>[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:30]=1[C:31]1[O:4][CH2:3][CH:2]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:7][CH:6]=2)[N:1]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 874382,6-Difluorobenzoyl chlorideHCID 19881301HCID 19881301, compound

Product 1

HCID 15007772HCID 15007772, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2.77 g (10 millimoles) of 2-amino-2-(4-n-decylphenyl)ethanol, 1.01 g (10 millimoles) of triethylamine and 30 ml of tetrahydrofuran contained in a 100 ml eggplant-shaped (spheroidal) flask, a solution of 1.77 g (10 millimoles) of 2,6-difluorobenzoyl chloride in 15 ml of tetrahydrofuran was added over 30 minutes with stirring at ice-bath temperature. After further continuation of stirring for 3 hours at room temperature, the produced triethylamine hydrochloride was removed by filtration using a glass filter and the filtrate was concentrated under reduced pressure. This concentrate was added with 50 ml of benzene and 3.57 g (30 millimoles) of thionyl chloride, and then refluxed for 3 hours with stirring on an oil bath. The reaction mixture was concentrated under reduced pressure and added with 50 ml of methanol followed by dropwise addition of 2 ml of a 50% aqueous sodium hydroxide solution at 60° C. with stirring. After further continuation of stirring for 30 minutes, the reaction mixture was poured into water and extracted with ethyl acetate followed by desiccation over anhydrous sodium sulfate and concentration under reduced pressure. This concentrate was purified by silica-gel column chromatography using a 8/2 solvent mixture of n-hexane/ethyl acetate as a movable phase to obtain 2-(2,6-difluorophenyl)-4-(4-n-decylphenyl)-2-oxazoline (Compound Number 20).

Workup

  1. stirringAfter further continuation of stirring for 3 hours at room temperature
  2. customthe produced triethylamine hydrochloride was removed by filtration
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. temperaturerefluxed for 3 hours
  6. stirringwith stirring on an oil bath
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. additionadded with 50 ml of methanol
  9. additionfollowed by dropwise addition of 2 ml of a 50% aqueous sodium hydroxide solution at 60° C.
  10. stirringwith stirring
  11. stirringAfter further continuation of stirring for 30 minutes
  12. additionthe reaction mixture was poured into water
  13. extractionextracted with ethyl acetate
  14. concentrationfollowed by desiccation over anhydrous sodium sulfate and concentration under reduced pressure
  15. customThis concentrate was purified by silica-gel column chromatography
  16. additiona 8/2 solvent mixture of n-hexane/ethyl acetate as a movable phase

Sources & evidence

ORD record
ord-652927ad55a847f085dbef2194a57ac3
Source dataset
uspto-grants-1992_08
Patent number
US05141948

Reaction notes

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