Acetone → HCID 178443597, compound

HRID 1437054Notes

Reaction equation

HRID 1437054 reaction equation
CO.Cl.Cl.[Cl:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:9][NH:10][C:11]([NH:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[NH:15])=[NH:12].[CH3:29][C:30]([CH3:32])=O>>[ClH:5].[CH2:17]([NH:16][C:14]1[NH:13][C:11]([NH:10][CH2:9][C:8]2[CH:25]=[CH:26][C:27]([Cl:28])=[C:6]([Cl:5])[CH:7]=2)=[N:12][C:30]([CH3:32])([CH3:29])[N:15]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443634HCID 178443634, compound

Product 1

HCID 178443597HCID 178443597, compound

Procedure

25 ml of methanol, 40 ml of acetone and 0.1 ml of concentrated hydrochloric acid were added to 1.8 g (4.4 mmol) of N1-(3′,4′-dichlorobenzyl)-N5-octyl-biguanide hydrochloride, and the mixture was refluxed for 24 hours. The solvent was distilled of f under reduced pressure, and the residue was dissolved in 80% aqueous acetonitrile. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.5 g of a colorless resinous solid (1) from the first main elution fraction with a mixture of chloroform and methanol (95:5), and 0.7 g of a colorless resinous solid (2) from the second main elution fraction.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. distillationThe solvent was distilled of f under reduced pressure
  3. dissolutionthe residue was dissolved in 80% aqueous acetonitrile
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1926e02dfbe940a98712f0090e47d628
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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