Acetic acid--water (1/1) → HCID 86672711, compound

HRID 2168534Notes

Reaction equation

HRID 2168534 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.O>ClCCCl>[O:2]=[CH:3][CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 86672710HCID 86672710, compound

Product 1

HCID 86672711HCID 86672711, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 1-(2,2-dimethoxyethyl)-2-phenyl-1H-benzo[d]imidazole-7-carboxylate (719 mg, 2.1 mmol) from Step A above was heated to reflux in 1:1 trifluoroacetic acetic acid/water (6 mL) and 1,2-dichloroethane (2 mL) for 2 h. The reaction mixture was concentrated, diluted with ethyl acetate, and pH adjusted to 8 with saturated aqueous sodium bicarbonate. The aqueous phase was extracted with additional ethyl acetate and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give methyl 1-(2-oxoethyl)-2-phenyl-1H-benzo[d]imidazole-7-carboxylate as a light pink solid (526 mg, 85%): 1H NMR (500 MHz, CDCl3) δ 9.80 (s, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 2H), 7.54-7.50 (m, 3H), 7.37 (d, J=7.5 Hz, 1H), 5.26 (s, 2H), 3.92 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous phase was extracted with additional ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2250b43be51e4473a5f276f255fd3f4f
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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