Triethylamine → HCID 15007757, compound

HRID 847369Notes

Reaction equation

HRID 847369 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1)O.C(N(CC)CC)C.[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30](Cl)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:39].[OH-].[Na+]>O1CCCC1.C1C=CC=CC=1>[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30]1[S:39][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=2)[CH2:2][N:1]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 27365472-Chloro-6-fluorobenzoyl chlorideHCID 15007756HCID 15007756, compound

Product 1

HCID 15007757HCID 15007757, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2.65 g (10 millimoles) of 2-amino-1-(4-n-octyloxyphenyl)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 1.93 g (10 millimoles) of 2-chloro-6-fluorobenzoyl chloride dissolved in 10 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. To this concentrate and 30 ml of toluene contained in a 100 ml eggplant-shaped flask, 4.44 g (20 millimoles) of phosphorus pentasulfide was added at once and refluxed for 4 hours on an oil bath with stirring. After cooling to room temperature, the reaction mixture was added with 40 ml of a 30% aqueous sodium hydroxide solution and stirred for 1 hour at room temperature. The reaction liquid was added with 100 ml of benzene and washed with a saturated aqueous sodium chloride solution followed by desiccation over anhydrous sodium sulfate and concentrated 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-chloro-6-fluorophenyl)-5-(4-n-octyloxyphenyl)-2-thiazoline (Compound Number 91).

Workup

  1. additionwas added over 30 minutes
  2. stirringAfter further continuation of stirring for 3 hours at room temperature
  3. customthe produced triethylamine hydrochloride was removed by filtration
  4. filtrationfilter
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. concentrationTo this concentrate
  7. custom30 ml of toluene contained in a 100 ml eggplant-shaped flask
  8. temperaturerefluxed for 4 hours on an oil bath
  9. stirringwith stirring
  10. stirringstirred for 1 hour at room temperature
  11. customThe reaction liquid
  12. washwashed with a saturated aqueous sodium chloride solution
  13. concentrationconcentrated under reduced pressure
  14. customThis concentrate was purified by silica-gel column chromatography
  15. additiona 8/2 solvent mixture of n-hexane/ethyl acetate as a movable phase

Sources & evidence

ORD record
ord-fcdcbc872f104d698e7ed3df01b6d192
Source dataset
uspto-grants-1992_08
Patent number
US05141948

Reaction notes

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