Ethanolamine → HCID 86622007, compound

HRID 1511199Notes

Reaction equation

HRID 1511199 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([CH2:17][NH2:18])[OH:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O.C(#N)C.CCOCC>[C:1](=[NH:18])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([OH:16])[CH3:17]

Participants

8

Reactant 4

HCID 700EthanolamineHCID 1140TolueneHCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 86622007HCID 86622007, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a 500 mL round bottom flask equipped with stirbar, Dean-Stark apparatus, reflux condenser, and N2 inlet was added benzophenone (45.5 g, 0.25 mol), ethanol amine (23 mL, 0.38 mol), p-toluenesulfonic acid (4.3 g, 0.025 mol), and toluene (300 mL). The reaction stirred at reflux for 16 hours, collecting 8 mL water. The solution was cooled and the solution washed with NaHCO3(aq) (2×400 mL). The aqueous layer was extracted with ether (2×300 mL) and the combined organic layers dried over MgSO4, stirred with carbon black for 1 hour, then filtered. The solvent was evaporated and the residue dissolved in ether (300 mL). Hexanes (900 mL) was added and the product crystallized over 2 hours at room temperature. The solid was filtered and recrystallized from 3:1 hexanes:ether giving 25.2 g of colorless needles (0.112 mol, 45%). HPLC (3:1 acetonitrile:water, C8 column) 99.9+% pure.

Workup

  1. customTo a 500 mL round bottom flask equipped with stirbar, Dean-Stark apparatus
  2. temperaturereflux condenser, and N2 inlet
  3. temperatureat reflux for 16 hours
  4. customcollecting 8 mL water
  5. temperatureThe solution was cooled
  6. washthe solution washed with NaHCO3(aq) (2×400 mL)
  7. extractionThe aqueous layer was extracted with ether (2×300 mL)
  8. dry with materialthe combined organic layers dried over MgSO4
  9. stirringstirred with carbon black for 1 hour
  10. filtrationfiltered
  11. customThe solvent was evaporated
  12. dissolutionthe residue dissolved in ether (300 mL)
  13. additionHexanes (900 mL) was added
  14. customthe product crystallized over 2 hours at room temperature
  15. filtrationThe solid was filtered
  16. customrecrystallized from 3:1 hexanes

Sources & evidence

ORD record
ord-0de1b783dde740d79f2cab55f12b12fa
Source dataset
uspto-grants-2012_07
Patent number
US08212083B2

Reaction notes

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