Acetone → HCID 178476230, compound

HRID 1437100Notes

Reaction equation

HRID 1437100 reaction equation
CO.Cl.Cl.Cl.[CH2:6]([NH:12][C:13]([NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[NH:17])=[NH:14])[C:7]1[O:11][CH:10]=[CH:9][CH:8]=1.[CH3:31][C:32]([CH3:34])=[O:33]>>[C:10]([OH:11])(=[O:33])[CH3:9].[CH3:31][C:32]1([CH3:34])[N:14]=[C:13]([NH:12][CH2:6][C:7]2[O:11][CH:10]=[CH:9][CH:8]=2)[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[N:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443248HCID 178443248, compound

Product 1

HCID 178476230HCID 178476230, compound

Procedure

150 ml of methanol, 120 ml of acetone and 0.6 ml of concentrated hydrochloric acid were added to 10.0 g (23.7 mmol) of N1-furfuryl-N5-dodecyl-biguanide dihydrochloride. The mixture was refluxed for 22 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and to the solution was added 11 ml of 5N sodium hydroxide. The mixture was stirred, washed with 10% aqueous sodium acetate, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (elution with a mixture of chloroform/methanol/acetic acid (9:1:1)) to obtain 8.4 g of a pale yellow resinous solid.

Workup

  1. temperatureThe mixture was refluxed for 22 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionto the solution was added 11 ml of 5N sodium hydroxide
  5. washwashed with 10% aqueous sodium acetate
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography (
  9. washelution
  10. additionwith a mixture of chloroform/methanol/acetic acid (9:1:1))

Sources & evidence

ORD record
ord-07acb953a29e4b35bf7ee8aa51c4f6e9
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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