Trifluoroacetic acid → (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

HRID 887382Notes

Reaction equation

HRID 887382 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC(OC)=CC=2)=[CH:14][CH:13]=1)=[O:11].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59327033HCID 59327033, compound

Product 1

HCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of compound (1H-benzo[d]imidazol-2-yl)(4-(4-methoxybenzyloxy)phenyl)methanone (268 g, 0.75 mol) in dichloromethane (2.7 L) at ambient temperature was added TFA (289 mL, 3.75 mol, 5.0 eq.) slowly using an addition funnel. The reaction was stirred at ambient temp for 16 h. LCMS analysis of the reaction mixture revealed that the reaction was complete. The reaction mixture was neutralized with satd. aqueous NaHCO3 to pH=7-8, and stirred for 20 minutes. The resulting solid was filtered and washed with water and dried under vacuum oven at 45° C. to give product.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried under vacuum oven at 45° C.
  4. customto give product

Sources & evidence

ORD record
ord-cb75ca0c866a41f1aacd96ff5b360c66
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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