Propionic Acid → HCID 178437463, compound

HRID 889186Notes

Reaction equation

HRID 889186 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](O)(=O)[CH2:25][CH3:26]>CN(C=O)C>[CH2:16]([O:9][C:3]1[C:2]2[NH:1][C:24]([CH2:25][CH3:26])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5799372,3-Diaminophenol

Product 1

HCID 178437463HCID 178437463, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2,3-diaminophenol (5 g, 40.3 mmol) was dissolved in propionic acid (10 mL) and stirred at 150° C. for 3 h. The reaction mixture was cooled to room temperature and the volume reduced under high vacuum to give a brown solid which was partitioned between chloroform and a saturated solution of bicarbonate, the chloroform layer was separated, dried and concentrated to give a brown solid. The brown solid (1.3 g, 8.0 mmol) was dissolved in DMF (40 mL) and K2CO3 (2.8 g, 0.02 mmol) was added followed by benzylbromide (1.5 g, 8.8 mmol). The reaction mixture was stirred at room temperature overnight, partitioned with water and ethyl acetate, ethyl acetate layer was separated, dried (MgSO4), concentrated, and purified by flash chromatography to give 7-benzyloxy-2-ethyl-1H-benzimidazole (0.9 g, 44%). LCMS 253 (M+)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto give a brown solid which
  3. customwas partitioned between chloroform
  4. customa saturated solution of bicarbonate, the chloroform layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give a brown solid
  8. stirringThe reaction mixture was stirred at room temperature overnight
  9. custompartitioned with water and ethyl acetate, ethyl acetate layer
  10. customwas separated
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. custompurified by flash chromatography

Sources & evidence

ORD record
ord-457c0676a63e47e0bf40c2d9756d86cc
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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