Formic Acid → HCID 178466779, compound

HRID 547637Notes

Reaction equation

HRID 547637 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:18])[CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[CH:19](O)=O>O1CCCC1>[NH:8]1[C:7]2[CH:6]=[CH:5][C:4]([O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]([OH:18])[CH3:17])=[CH:12][CH:11]=3)=[CH:3][C:2]=2[N:1]=[CH:19]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 57585929HCID 57585929, compound

Product 1

HCID 178466779HCID 178466779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 1-{4-[(3,4-diaminophenyl)oxy]phenyl}ethanol was dissolved in 10 mL of tetrahydrofuran and 5 mL of 88% formic acid and heated at 100 degrees Centigrade for 2 hours. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate and saturated NaHCO3. The organic layer was separated and washed twice with saturated NaHCO3. The organic layer was dried over MgSO4 and concentrated. The residue was dissolved in 10 mL of THF and heated at 100 degrees centigrade with 5 mL of aqueous 10% LiOH for 2 hours. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated to give crude 1-[4-(1H-benzimidazol-5-yloxy)phenyl]ethanol, which was carried on crude to the next step without further purification. (M+1) 239.0, 1.39 min (LC/MS method B)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. customThe organic layer was separated
  4. washwashed twice with saturated NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 10 mL of THF
  8. temperatureheated at 100 degrees centigrade with 5 mL of aqueous 10% LiOH for 2 hours
  9. additionThe reaction mixture was diluted with water
  10. extractionextracted three times with ethyl acetate
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-280de2b6278440f29ded56943f17050d
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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