Triethylamine → 4-methoxy-1H-benzo[d]imidazol-2(3H)-one

HRID 2191999Notes

Reaction equation

HRID 2191999 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.P(N=[N+]=[N-])(=O)([O:21][C:22]1C=CC=CC=1)OC1C=CC=CC=1.C([N:34](CC)CC)C>C1COCC1>[CH3:12][O:11][C:10]1[C:2]2[NH:1][C:22](=[O:21])[NH:34][C:3]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 129266284-methoxy-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottomed flask was added 2-amino-3-methoxybenzoic acid (2.2705 g, 13.58 mmol), diphenyl phosphorazidate (3.51 mL, 16.30 mmol), and triethylamine (3.79 mL, 27.2 mmol) in THF to stir at 80° C. Upon completion the reaction was allowed to cool to room temperature. Solvent was evaporated. The residue was taken up in DCM. The reaction mixture was diluted with water and extracted with DCM. A white precipitate was noted to form during extraction The solid was filtered to provide 4-methoxy-1H-benzo[d]imidazol-2(3H)-one. [M+H]=165.0.

Workup

  1. temperatureto cool to room temperature
  2. customSolvent was evaporated
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with DCM
  5. customto form during extraction The solid
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-91e43439c5174e1b80954496d25dc5f7
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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