Acetone → HCID 178443385, compound

HRID 1437055Notes

Reaction equation

HRID 1437055 reaction equation
CO.[ClH:3].Cl.Cl.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[NH:19])=[NH:16])=[CH:10][CH:9]=1.[CH3:31][C:32]([CH3:34])=O>>[ClH:3].[NH2:16][C:15]1[N:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=2)[C:32]([CH3:34])([CH3:31])[N:19]=[C:18]([NH: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 178443401HCID 178443401, compound

Product 1

HCID 178443385HCID 178443385, compound

Procedure

50 ml of methanol, 40 ml of acetone and 0.2 ml of concentrated hydrochloric acid were added to 1.5 g (3.6 mmol) of N1-(4-methoxyphenyl)-N5-decyl-biguanide dihydrochloride, and the mixture was refluxed for 20 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1)). The eluate was dissolved in 80% aqueous acetonitrile, and the solvent was distilled off under reduced pressure, followed by sufficient drying under reduced pressure to obtain 0.92 g of a pale yellow resinous solid.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (
  4. washelution
  5. additionwith a mixture of chloroform and methanol (9:1))
  6. dissolutionThe eluate was dissolved in 80% aqueous acetonitrile
  7. distillationthe solvent was distilled off under reduced pressure
  8. customby sufficient drying under reduced pressure

Sources & evidence

ORD record
ord-e64468651e9444d7918cec9edf74865a
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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