Acetic Acid → HCID 53657667, compound

HRID 1276917Notes

Reaction equation

HRID 1276917 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][NH:12][C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=O)[CH3:22])=[C:16]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[CH:15]=1>CO>[CH3:22][C:21]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[C:16]2[CH:15]=[C:14]([C:13](=[O:35])[NH:12][CH2:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=3)[CH:19]=[CH:18][C:17]=2[N:20]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18315487HCID 18315487, compound

Product 1

HCID 53657667HCID 53657667, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Two milliliters of acetic acid and 5 ml of methanol were added to 0.490 g of N-(2-pyridylmethyl)-4-acetylamino-3-(3,4-methylenedioxybenzylamino)benzamide, and the mixture was stirred at 70° C. for 8 hours. The reaction solution was concentrated under reduced pressure. The residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1), and was then crystallized from ethyl acetate. The crystals were separated through filtration, and were dried to give 0.270 g of 2-methyl-1-(3,4-methylenedioxybenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (243).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified through silica-gel column chromatography (eluent
  3. additiona mixture of ethyl acetate and methanol at a ratio of 9:1), and
  4. customwas then crystallized from ethyl acetate
  5. customThe crystals were separated through filtration
  6. customwere dried

Sources & evidence

ORD record
ord-c016cb6d74334faa95b96cf4c1cf7e85
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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