Hydrochloric Acid → methyl 1H-1,3-benzodiazole-2-carboxylate

HRID 1850249Notes

Reaction equation

HRID 1850249 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].ClC(Cl)(Cl)[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1.Cl.[CH3:21]O>>[CH3:21][O:4][C:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[O:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 77133Benzimidazole, 2-trichloromethyl-

Product 1

HCID 576526methyl 1H-1,3-benzodiazole-2-carboxylateYield 83%

Procedure

Na2CO3 (0.64 g, 6.07 mmol) was added to a solution of (17) (1.9 g, 6.07 mmol) in 20 mL MeOH. The reaction mixture was heated to reflux for 14 h and then cooled to RT. 1N HCl was added to the solution and the reaction mixture was stirred for 0.5 hour. The mixture was extracted with EA. The organic phase was washed with brine, dried over Na2SO4 and evaporated to give the title compound (0.89 g, yield 83%). ESI-MS (M+1): 177 calc. for C9H8N2O2 176.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. extractionThe mixture was extracted with EA
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-fb6394ef79624fdf8729eb991c24e1a5
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

Loading…