Triethylamine → HCID 14853164, compound

HRID 1110789Notes

Reaction equation

HRID 1110789 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:24]=1[C:25](Cl)=O>O1CCCC1>[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:24]=1[C:25]1[O:4][CH2:3][CH:2]([C:5]2[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27365472-Chloro-6-fluorobenzoyl chlorideHCID 14853163b-AMino-4-tert-butylbenzeneethanol

Product 1

HCID 14853164HCID 14853164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A 100 ml eggplant-shaped flask was charged with 1.4 g (7.25 millimoles) of 2-amino-2-(4-t-butylphenyl)-1-ethanol and 0.73 g (7.25 millimoles) of triethylamine and 30 ml of tetrahydrofuran, and a solution of 1.4 g (7.25 millimoles) of 2-chloro-6-fluorobenzoyl chloride in 10 ml of tetrahydrofuran was added over 30 minutes to the flask with ice cooling and stirring. The mixture was stirred further for 3 hours at room temperature. The resulting triethylamine hydrochloride was removed by a glass filter, and the filtrate was concentrated under reduced pressure. The concentrate, thionylchloride (2.6 g; 21.8 and 50 ml of benzene were put in a 200 ml egg-plant-shaped flask, and refluxed for 5 hours. The reaction mixture was concentrated under reduced pressure. Fifty milliliters of methanol was added to the remaining oil, and the mixture was heated to 60° C. To the mixture was added dropwise 5 ml of a 15 % aqueous solution of sodium hydroxide. After the addition, the mixture was stirred at the same temperature for 1 hour, transferred into water, and extracted with ethyl acetate. The extract was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=8/2) to give 2-(2-chloro-6-fluorophenyl)-4-(4-t-butylphenyl)-2-oxazoline (compound No. 45) as a colorless oil. Yield 1.8 g (74.9 %).

Workup

  1. stirringThe mixture was stirred further for 3 hours at room temperature
  2. customThe resulting triethylamine hydrochloride was removed by a glass
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. custom21.8 and 50 ml of benzene were put in a 200 ml egg-plant-shaped flask
  6. temperaturerefluxed for 5 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. additionFifty milliliters of methanol was added to the remaining oil
  9. additionTo the mixture was added dropwise 5 ml of a 15 % aqueous solution of sodium hydroxide
  10. additionAfter the addition
  11. stirringthe mixture was stirred at the same temperature for 1 hour
  12. extractionextracted with ethyl acetate
  13. customThe extract was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-468a1e570e194522b7a3a0cba9bd1dfc
Source dataset
uspto-grants-1990_12
Patent number
US04977171

Reaction notes

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