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

HRID 1880081Notes

Reaction equation

HRID 1880081 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. MS (ESI, pos. ion) m/z: 165.0 (M+1).

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-45ef1813a7544f90addd045b92697ed2
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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