Acetone → HCID 178443595, compound

HRID 1437102Notes

Reaction equation

HRID 1437102 reaction equation
CO.[ClH:3].Cl.Cl.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([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:7]=1.[CH3:31][C:32]([CH3:34])=O>>[ClH:3].[ClH:3].[NH2:18][C:17]1[N:16]([C:8]2[CH:7]=[N:6][C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:32]([CH3:34])([CH3:31])[N:21]=[C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:19]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 887MethanolHCID 178443628HCID 178443628, compound

Product 1

HCID 178443595HCID 178443595, compound

Procedure

150 ml of methanol, 120 ml of acetone and 0.5 ml of concentrated hydrochloric acid were added to 7.0 g (18.6 mmol) of N1-(3-quinolyl)-N5-octyl-biguanide dihydrochloride. The mixture was refluxed for 26 hours, and 1.8 ml of concentrated hydrochloric acid was further added thereto. The mixture was refluxed for 22 hours, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1)) to obtain 5.3 g of a pale yellow powder.

Workup

  1. temperatureThe mixture was refluxed for 26 hours
  2. temperatureThe mixture was refluxed for 22 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (
  5. washelution
  6. additionwith a mixture of chloroform and methanol (9:1))

Sources & evidence

ORD record
ord-5a6dc13a7750465a9bd85f527dd10513
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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