Trifluoroacetic acid → HCID 22419132, compound

HRID 1720572Notes

Reaction equation

HRID 1720572 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]3[C:26](=[O:33])[C:27]([CH3:32])=[C:28]([CH3:31])[C:29](=[O:30])[C:24]=3[N:23]=[C:22]2[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:16][CH:15]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[C:25]3[C:26](=[O:33])[C:27]([CH3:32])=[C:28]([CH3:31])[C:29](=[O:30])[C:24]=3[N:23]=[C:22]2[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:18][CH:19]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22419172HCID 22419172, compound

Product 1

HCID 22419132HCID 22419132, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

420 mg (0.8 mmol) Of the ester was dissolved in 20 ml of chloroform, and to this was added 4 ml of trifluoroacetic acid and the mixture was heated under reflux for 2 hours. After the reaction mixture was cooled, an aqueous saturated solution of sodium bicarbonate was added to adjust pH to 8. The organic layer was washed with an aqueous saturated saline solution and dried over anhydrous sodium sulphate, and the solvent was distilled off under the reduced pressure to obtain 370 mg of 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-n-butyl-5,6-dimethyl-1H-benzimidazol-4,7-dione (Compound No. 26) as yellow powder (yield 99% ). This has the following NMR spectrum. δ ppm (CDCl3): 0.83 (3H, t, J=7 Hz), 1.27-1.35 (2H, m), 1.57-1.70 (2H, s), 2.09 (3H, s), 2.71 (2H, t, J=8 Hz), 5.61 (2H, s), 7.10 (2H, d, J=8 Hz), 7.31 (3H, d, J=8 Hz), 7.40-7.46 (1H, m), 7.55 (1H, dd, J=8, 1 Hz), 7.95 (1H, dd, J=8, 1 Hz)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter the reaction mixture was cooled
  4. washThe organic layer was washed with an aqueous saturated saline solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. distillationthe solvent was distilled off under the reduced pressure

Sources & evidence

ORD record
ord-de5700f2d27f4b26b62b41214cef2ddf
Source dataset
uspto-grants-1996_04
Patent number
US05506361

Reaction notes

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