Acetone → HCID 178443392, compound

HRID 1437045Notes

Reaction equation

HRID 1437045 reaction equation
CO.[ClH:3].Cl.Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:11][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]CC)=[NH:17])=[NH:14].[CH3:36][C:37]([CH3:39])=O>>[ClH:3].[CH3:36][C:37]1([CH3:39])[N:14]=[C:13]([NH:12][CH2:11][C:10]2[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:8]([O:7][CH3:6])[CH:9]=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][CH3:28])=[N:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443249HCID 178443249, compound

Product 1

HCID 178443392HCID 178443392, compound

Procedure

75 ml of methanol, 120 ml of acetone and 0.2 ml of concentrated hydrochloric acid were added to 3.5 g (7.5 mmol) of N1-(3,4-dimethoxybenzyl)-N5-dodecyl-biguanide dihydrochloride, and the mixture was refluxed for 24 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 (9:1.2)), and dissolved in 70% aqueous acetonitrile. The solution was concentrated under reduced pressure to remove the solvent, and the residue was sufficiently dried under reduced pressure to obtain 2.2 g of a colorless resinous solid.

Workup

  1. temperaturethe mixture was refluxed for 24 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 (9:1.2)), and
  6. dissolutiondissolved in 70% aqueous acetonitrile
  7. concentrationThe solution was concentrated under reduced pressure
  8. customto remove the solvent
  9. customthe residue was sufficiently dried under reduced pressure

Sources & evidence

ORD record
ord-0411574462a34a6eb6c5eba00a17b883
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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