Acetone → HCID 178443599, compound

HRID 1437050Notes

Reaction equation

HRID 1437050 reaction equation
CO.[CH3:3][C:4]([CH3:6])=O.[ClH:7].Cl.Cl.[OH:10][C:11]1[CH:32]=[CH:31][C:14]([CH2:15][NH:16][C:17]([NH:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[NH:21])=[NH:18])=[CH:13][CH:12]=1>C(#N)C>[ClH:7].[CH2:23]([NH:22][C:20]1[NH:19][C:17]([NH:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([OH:10])=[CH:32][CH:31]=2)=[N:18][C:4]([CH3:6])([CH3:3])[N:21]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443636HCID 178443636, compound

Product 1

HCID 178443599HCID 178443599, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

25 ml of methanol, 40 ml of acetone and 0.1 ml of concentrated hydrochloric acid were added to 16 g (4.6 mmol) of N1-(4-hydroxybenzyl)-N5-octyl-biguanide dihydrochloride, and the mixture was stirred at 40° C. for 63 hours, and refluxed for 8 hours. The solvent was distilled off under reduced pressure, to give a residue, which was dissolved in 80% aqueous acetonitrile. 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 (8:2)) to obtain 16 g of a colorless resinous solid.

Workup

  1. temperaturerefluxed for 8 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customto give a residue, which
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (
  6. washelution
  7. additionwith a mixture of chloroform and methanol (8:2))

Sources & evidence

ORD record
ord-6672607c5c69494c81bca3eb5338479a
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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