Acetic Acid → HCID 67273117, compound

HRID 1698548Notes

Reaction equation

HRID 1698548 reaction equation
[NH:1]([C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[NH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1)[NH2:2].CCC(=O)[CH2:17][C:18](=O)[CH2:19][CH3:20].[C:23](=O)([O-])O.[Na+].[C:28](O)(=O)[CH3:29]>>[CH2:28]([N:2]1[CH2:17][C:18]([CH2:19][CH3:20])=[CH:23][N:1]1[C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[NH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:29]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 819233,5-HeptanedioneHCID 516892Sodium BicarbonateHCID 55281788HCID 55281788, compound

Product 1

HCID 67273117HCID 67273117, compoundYield 83%

Conditions

Temperature
100 °C

Procedure

To a suspension of 211 mg (0.986 mmol) of 7-hydrazino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one in 2 mL of acetic acid was added 0.13 mL (0.986 mmol) of 3,5-heptanedione, the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 50-80% ethylacetate/n-hexane gradient mixture to give 221 mg (83%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 50-80% ethylacetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-3615a679bc0c430b89a80908601b4a6b
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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