Hydrochloric Acid → HCID 178498030, compound

HRID 2064241Notes

Reaction equation

HRID 2064241 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Cl:13])[C:11]=1[NH2:12])[C:6]([O-:8])=[O:7].[C:14](CC(=O)C)(=O)[CH3:15].[CH2:21](O)C>>[Cl:13][C:10]1[C:11]2[NH:12][C:14]([CH3:15])=[N:2][C:3]=2[CH:4]=[C:5]([C:6]([O:8][CH3:21])=[O:7])[CH:9]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 31261AcetylacetoneHCID 86653286HCID 86653286, compound

Product 1

HCID 178498030HCID 178498030, compoundYield 59%

Procedure

Add 2N hydrochloric acid (8 mL) to a solution of 3,4-diamino-5-chlorobenzoate (from acid preparation 1, 435 mg, 2.17 mmol) in ethanol (20 mL). Heat the mixture to reflux then add acetylacetone (437 mg, 4.37 mmol) to the yellow solution. The yellow solution turned purple upon addition. Stir at reflux for 1 hour and the solution turned back to yellow. Stir at reflux for an additional 1 hour. Concentrate the solvent to a colorless residue. Add water (20 mL). Extract the suspension with ethyl acetate (20 mL). Basify the aqueous layer with 2N sodium hydroxide (˜8 mL) to pH˜10. Extract with ethyl acetate (3×15 mL). Wash combined organics from the basic extraction with brine (5 mL). Dry over magnesium sulfate, filter, concentrate, and dry under high vacuum to yield methyl 7-chloro-2-methyl-1H-benzo[d]imidazole-5-carboxylate (290 mg, 59%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.68 (s, 3H), 3.93 (s, 3H), 7.25 (s, 1H), 7.96 (s, 1H).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. additionThe yellow solution turned purple upon addition
  4. temperatureat reflux for 1 hour
  5. stirringStir
  6. temperatureat reflux for an additional 1 hour
  7. concentrationConcentrate the solvent to a colorless residue
  8. extractionExtract the suspension with ethyl acetate (20 mL)
  9. extractionExtract with ethyl acetate (3×15 mL)
  10. washWash
  11. extractioncombined organics from the basic extraction with brine (5 mL)
  12. dry with materialDry over magnesium sulfate
  13. filtrationfilter
  14. concentrationconcentrate
  15. customdry under high vacuum

Sources & evidence

ORD record
ord-8f298dc15fcf41398a1ccb94c9aa887b
Source dataset
uspto-grants-2012_10
Patent number
US08288405B2

Reaction notes

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