Triethylamine → HCID 18468853, compound

HRID 2229743Notes

Reaction equation

HRID 2229743 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2.C(N(CC)CC)C.[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>ClCCl>[CH:4]12[CH2:9][CH:7]([CH:6]=[CH:5]1)[CH2:8][CH:3]2[CH2:2][NH:1][S:19]([CH2:17][CH3:18])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 2471821-(Bicyclo[2.2.1]hept-5-en-2-yl)methanamine

Product 1

HCID 18468853HCID 18468853, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An oven-dried, nitrogen-flushed 1 L round bottom flask equipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar was charged with 116.3 g 5-aminomethylnorbornene (0.944 mol,) 95.5 g triethylamine (0.944 mol,) and 1 L dichloromethane. The addition funnel was charged with 121.4 g ethanesulfonyl chloride (0.944 mol,) and 500 ml dichloromethane. The contents of the addition funnel were added dropwise to the flask over the course of approx. two hours. During this time, the reaction warmed gradually and finally began a gentle reflux. The reaction was left to stir for approx. 24 hours. The mixture was transferred into a separatory funnel, and the organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate, and twice more with 300 ml water. The organic layer was dried over magnesium sulfate, then concentrated to yield an oil. Attempts to crystallize the oil from hexane:ethyl acetate failed. Silica gel column chromatography using hexane:ethyl acetate (60:40) as the eluent gave a clear, straw-colored oil that was further purified by vacuum distillation (140° C. at 5 microns of Hg) to provide 170 g of the desired ethanesulfonamide as a mixture of isomers. The product was identified by 1H and 13C NMR and IR spectroscopy.

Workup

  1. customAn oven-dried, nitrogen-flushed 1 L round bottom flask
  2. customequipped with an addition funnel, nitrogen inlet, reagent inlet, and a teflon-coated stir bar
  3. additionThe contents of the addition funnel were added dropwise to the flask over the course of approx. two hours
  4. temperatureDuring this time, the reaction warmed gradually
  5. waitThe reaction was left
  6. customThe mixture was transferred into a separatory funnel
  7. washthe organic layer was washed twice with 300 ml water, 2× with 300 mL dilute sodium bicarbonate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customto yield an oil
  11. customto crystallize the oil from hexane
  12. customgave a clear, straw-colored oil that
  13. distillationwas further purified by vacuum distillation (140° C. at 5 microns of Hg)

Sources & evidence

ORD record
ord-81abb115af4a4967a34067ef18d4744f
Source dataset
uspto-grants-2002_07
Patent number
US06420503B1

Reaction notes

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