Tetrahydrofuran → HCID 178519705, compound

HRID 547611Notes

Reaction equation

HRID 547611 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[CH2:18]1COCC1>C(O)=O>[NH:8]1[C:7]2[CH:6]=[CH:5][C:4]([O:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=3)=[CH:3][C:2]=2[N:1]=[CH:18]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57585853HCID 57585853, compound

Product 1

HCID 178519705HCID 178519705, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

{4-[(3,4-diaminophenyl)oxy]phenyl}methanol (3.21 g of crude material) was dissolved in 20 ml THF and 10 ml of formic acid. The reaction was heated in a 100 degree Centigrade oil bath for approximately 22 hours. The reaction was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed 5 times with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in 30 ml of THF and 10 ml of 10% aqueous LiOH and heated at 100 degrees Centigrade for 30 minutes. The reaction was diluted with water and ethyl acetate. The organic layer was washed with brine three times, dried over MgSO4, and concentrated under reduced pressure onto basic alumina. The compound was purified by silica gel column chromatography (100% dichloromethane to 10% (2M NH3 in methanol) in dichloromethane gradient) to give 1.26 g of [4-(1H-benzimidazol-5-yloxy)phenyl]methanol.

Workup

  1. temperatureThe reaction was heated in a 100 degree Centigrade oil bath for approximately 22 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed 5 times with saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 30 ml of THF
  8. temperature10 ml of 10% aqueous LiOH and heated at 100 degrees Centigrade for 30 minutes
  9. additionThe reaction was diluted with water and ethyl acetate
  10. washThe organic layer was washed with brine three times
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure onto basic alumina
  13. customThe compound was purified by silica gel column chromatography (100% dichloromethane to 10% (2M NH3 in methanol) in dichloromethane gradient)

Sources & evidence

ORD record
ord-f3e3815bebaa43adbb941581544a920f
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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