Toluene → HCID 67954229, compound

HRID 456187Notes

Reaction equation

HRID 456187 reaction equation
[CH2:1](O)[CH3:2].[F:4][C:5]([F:11])([F:10])[S:6]([NH2:9])(=[O:8])=[O:7].[C:12]12([C:22]([OH:24])=[O:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:12]12([C:22]([O:24][CH2:1][CH2:2][NH:9][S:6]([C:5]([F:11])([F:10])[F:4])(=[O:8])=[O:7])=[O:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 132351-Adamantanecarboxylic acidHCID 86666433HCID 86666433, compound

Product 1

HCID 67954229HCID 67954229, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

100 g (0.52 mol) of trifluoromethanesulfonamide ethanol, 108.6 g (0.54 mol) of 1-adamantanecarboxylic acid, 0.1 mol of para-toluenesulfonic acid and 500 g of toluene were added to a glass flask equipped with a thermometer and a condenser, followed by dehydration using a dean-stark dehydration apparatus under reflux. After 9 hours of reflux, about 9 ml of water was removed. The resulting reaction solution was dissolved in 500 g of ethyl acetate, and washing was conducted twice with a saturated sodium hydrogencarbonate solution, once with a 1N—HCl and once with a saturated saline solution in this order. Then, the organic phase was dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant was subjected to recrystallization in hexane, thereby obtaining 140 g of N-[2-(adamantan-1-ylcarbonyloxy)ethyl]trifluoromethanesulfonamide (yield: 75%, purity: 99%).

Workup

  1. customequipped with a thermometer and a condenser
  2. temperatureunder reflux
  3. temperatureAfter 9 hours of reflux
  4. customabout 9 ml of water was removed
  5. customThe resulting reaction solution
  6. washwashing
  7. dry with materialThen, the organic phase was dried with sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant was subjected to recrystallization in hexane

Sources & evidence

ORD record
ord-6e6bb64c0b754d50a4dee93d866de3de
Source dataset
uspto-grants-2013_07
Patent number
US08497395B2

Reaction notes

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