Hydrochloric Acid → 5-Methylbenzimidazolone

HRID 501798Notes

Reaction equation

HRID 501798 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1C(O)=O.C([O:15][CH2:16]C)(=O)C.O.Cl.C([N:22](CC)CC)C>O1CCOCC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:16](=[O:15])[NH:22][C:3]=2[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 2231345-Methylbenzimidazolone

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 199401P,P-Diphenylphosphinic azideSolvent

Procedure

4.00 g of 2-amino-5-methylbenzoic acid was dissolved in 40 mL of 1,4-dioxane, to which 5.5 mL of triethylamine and 6.8 mL of diphenylphosphoryl azide were successively added, and this mixture was stirred for 1.5 hours while heating it under reflux. The reaction mixture, to which a mixture of ethyl acetate and water was added, was adjusted to pH 7 with 1M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure to yield 2.96 g of 5-methyl-1,3-dihydro-2H-benzimidazol-2-one as light yellow solid.

Workup

  1. additionwere successively added
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. additionwas added
  5. customthe organic phase was separated
  6. washAfter the resultant organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-fab17d724e3842a1b89b8960d73c792c
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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