Toluene → HCID 67954229, compound

HRID 1753665Notes

Reaction equation

HRID 1753665 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

A glass flask fitted with a thermometer and a condenser was charged with 100 g (0.52 mol) of trifluoromethanesulfonamide ethanol, 108.6 g (0.54 mol) of 1-adamantanecarboxylic acid, para-toluenesulfonic acid (0.1 mol) and 500 g of toluene, and a Dean-Stark dehydration apparatus was used to perform dehydration under reflux conditions. Refluxing for 9 hours enabled removal of approximately 9 ml of water. The resulting reaction mixture was dissolved in 500 g of ethyl acetate, and the thus obtained solution was washed twice with a saturated solution of sodium bicarbonate, once with 1N—HCl, and once with a saturated solution of sodium chloride. The organic phase was then dried over sodium sulfate, the solvent was removed by distillation under reduced pressure, and the product was recrystallized in hexane, yielding 140 g of N-[2-(adamantan-1-ylcarbonyloxy)ethyl]trifluoromethanesulfonamide (yield: 75%, purity: 99%).

Workup

  1. customA glass flask fitted with a thermometer and a condenser
  2. temperatureRefluxing for 9 hours
  3. customremoval of approximately 9 ml of water
  4. customThe resulting reaction mixture
  5. washthe thus obtained solution was washed twice with a saturated solution of sodium bicarbonate, once with 1N—HCl
  6. dry with materialThe organic phase was then dried over sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customthe product was recrystallized in hexane

Sources & evidence

ORD record
ord-cb3677f1a9b14d20b6bfb68ffca942db
Source dataset
uspto-grants-2015_10
Patent number
US09164380B2

Reaction notes

Loading…