Hydrochloric Acid → HCID 21833745, compound

HRID 1741074Notes

Reaction equation

HRID 1741074 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[NH:10])OC)=[CH:5][C:4]=1[CH3:13].CO[CH:16](OC)[CH2:17][NH2:18].Cl.OS(O)(=O)=O>CO.O.[OH-].[Na+]>[Br:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]2[NH:18][CH:17]=[CH:16][N:10]=2)=[CH:5][C:4]=1[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 21833811HCID 21833811, compound

Product 1

HCID 21833745HCID 21833745, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-bromo-3-methylbenzimidate hydrochloride (D87, 5.0 g; 21.9 mmol) was dissolved in methanol (30 ml) and stirred during the addition of a solution of 2-aminoacetaldehyde dimethyl acetal (2.4 ml; 21.9 mmol) in methanol (10 ml) over 30 minutes. Stirring was continued for 36 hours and evaporated in vacuo to yield an orange gum (7 g crude). This crude hydrochloride was treated with conc. H2SO4 (12 ml) at 5°, the heated at 50° for 10 minutes. The solution was cooled in ice, diluted with H2O and basified with 10% NaOH. The aqueous solution was extracted with chloroform (4 times) and the organics combined, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by flash silica gel chromatography eluting with 1% MeOH/CHCl3 to yield the title compound as a white solid (1.55 g; 44%).

Workup

  1. customevaporated in vacuo
  2. customto yield an orange gum (7 g crude)
  3. temperaturethe heated at 50° for 10 minutes
  4. temperatureThe solution was cooled in ice
  5. extractionThe aqueous solution was extracted with chloroform (4 times)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash silica gel chromatography
  10. washeluting with 1% MeOH/CHCl3

Sources & evidence

ORD record
ord-2124b5f0d384421ca3b6d6efb2c12d6b
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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