Hydrochloric Acid → HCID 17816488, compound

HRID 2249696Notes

Reaction equation

HRID 2249696 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[C:8]([Br:16])=[CH:7][C:3]=1C(O)=O.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.Cl>O1CCOCC1.O.C(OCC)(=O)C>[Br:11][C:10]1[C:2]2[NH:1][C:22](=[O:31])[NH:19][C:3]=2[CH:7]=[C:8]([Br:16])[C:9]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17816503HCID 17816503, compound

Product 1

HCID 17816488HCID 17816488, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In 10 ml of dioxane is added 1.00 g of 2-amino-3,5-dibromo-4-(methoxycarbonyl)benzoic acid, to which are successively added 0.6 ml of triethylamine and 0.9 ml of diphenyl phosphoryl azide. The mixture thus obtained is heated under reflux for 1.5 hours. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 6 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 0.96 g of methyl 4,6-dibromo-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate is obtained as a light brown-colored solid product.

Workup

  1. customThe mixture thus obtained
  2. temperatureis heated
  3. temperatureunder reflux for 1.5 hours
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-659a4e6a416b43c181db6a23ef538a41
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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