Water → methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylate

HRID 43810Notes

Reaction equation

HRID 43810 reaction equation
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:9]=2[NH:8]1.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1>[Cl:3][C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:9]=2[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 22745204HCID 22745204, compound

Product 1

HCID 68407476methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylateYield 70.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Phosphorus oxychloride (8.5 g, 55.6 mmol) was added to methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (1.03 g, 5.36 mmol) (reference: WO 2006/116412 A2), and the mixture was stirred at 85° C. for four hours. The reaction solution was diluted with ethyl acetate and THF, slowly added to cold water and neutralized with sodium bicarbonate. The separated organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was dissolved in toluene and the insoluble matter was removed. Concentration under reduced pressure gave 800 mg of the title compound as an oily substance. The resulting compound was used for the next reaction without purification.

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. dissolutionthe residue was dissolved in toluene
  5. customthe insoluble matter was removed
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1d427edb06c84a3bbcf90349f410268a
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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