Ethanol → HCID 59304998, compound

HRID 2240231Notes

Reaction equation

HRID 2240231 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:17]=[C:16]([F:18])[C:12](C(O)=O)=[C:11]([F:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-]=[N+]=[N-].C([N:32]([CH2:35]C)CC)C.[CH2:37]([OH:39])[CH3:38].[O:40]1CCOCC1>ClCCl.CCCCC>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:17]=[C:16]([F:18])[C:12]([NH:32][C:35](=[O:40])[O:39][CH2:37][CH3:38])=[C:11]([F:19])[CH:10]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 33558AzideHCID 59305017HCID 59305017, compound

Product 1

HCID 59304998HCID 59304998, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

2.60 g (7.36 mmol) of 4-(dibenzylamino)-2,6-difluorobenzoic acid are dissolved in 20 ml of dioxane. 2.42 g (8.83 mmol) of diphenylphosphyl azide and then 1.08 g (10.7 mmol) of triethylamine are added dropwise, and the mixture is stirred at RT for one hour. 6.0 ml of ethanol are then added, and the mixture is heated under reflux for 2 hours. The reaction solution is then concentrated and the residue is dissolved in dichloromethane. The solution is washed with semiconcentrated sodium bicarbonate solution and water and dried over sodium sulfate, and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (mobile phase: dichloromethane). The oil obtained is dissolved in a little dichloromethane. Addition of a little pentane and scratching yields crystals which are filtered off with suction.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution is then concentrated
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washThe solution is washed with semiconcentrated sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (mobile phase: dichloromethane)
  9. customThe oil obtained
  10. customscratching yields crystals which
  11. filtrationare filtered off with suction

Sources & evidence

ORD record
ord-c841793264de42f98dbf2cef922990f4
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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