Water → HCID 86672715, compound

HRID 2369917Notes

Reaction equation

HRID 2369917 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:9]2[C:10]([C:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:17].O.[C:21](O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]=[C:6]1[NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:21])=[O:15])[C:9]=2[N:5]1[CH2:4][CH:3]=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86672716HCID 86672716, compound

Product 1

HCID 86672715HCID 86672715, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 3-(2,2-dimethoxyethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (0.4 g, 1.4 mmol) in methylene chloride (10 mL) with water (3 mL) and TFA (3 mL) was stirred at room temperature for 1.5 h. The reaction mixture was concentrated under reduced pressure to remove the excess trifluoroacetic acid, diluted with methylene chloride, washed with saturated aqueous sodium bicarbonate, re-extracted with methylene chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to give methyl 2-oxo-3-(2-oxoethyl)-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (0.2 g, 61%): 1H NMR (500 MHz, DMSO-d5) δ 11.43 (s, 1H), 9.61 (s, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 7.12-7.09 (m, 1H), 4.95-4.94 (m, 2H), 3.79 (s, 3H); MS (ESI+) m/z 234 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the excess trifluoroacetic acid
  3. additiondiluted with methylene chloride
  4. washwashed with saturated aqueous sodium bicarbonate
  5. extractionre-extracted with methylene chloride
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d6ba0cdb8c14edab1034509c5747c51
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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