Toluene → HCID 67954229, compound

HRID 1468602Notes

Reaction equation

HRID 1468602 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 under reflux using a dean-stark dehydration apparatus. 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-c6ebe05100a34b89b9413dfa7d34134d
Source dataset
uspto-grants-2015_04
Patent number
US09005872B2

Reaction notes

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