Methyl 2-amino-3-[(methoxyacetyl)amino]benzoate → methyl 2-(methoxymethyl)-1H-benzo[d]imidazole-4-carboxylate

HRID 1505770Notes

Reaction equation

HRID 1505770 reaction equation
[NH2:1][C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(O)(=O)C>[CH3:16][O:15][CH2:14][C:13]1[NH:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[N:1]=1

Participants

3

Reactant 1

HCID 90229318Methyl 2-amino-3-[(methoxyacetyl)amino]benzoate

Product 1

HCID 86721359methyl 2-(methoxymethyl)-1H-benzo[d]imidazole-4-carboxylateYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-amino-3-[(methoxyacetyl)amino]benzoate (280 mg) was dissolved in acetic acid (6 mL), and the solution was heated at 100° C. for 0.5 hour with stirring. After cooling the reaction mixture to room temperature, acetic acid was removed. To the residue was added saturated aqueous sodium bicarbonate under ice-cooling, and it was extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the titled compound (241 mg) as pale yellow powder.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. customacetic acid was removed
  3. additionTo the residue was added saturated aqueous sodium bicarbonate under ice-
  4. temperaturecooling
  5. extractionit was extracted with ethyl acetate
  6. washThe organic layer was washed sequentially with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-53d4375e1c994c2ea8002c57481917d9
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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