Acetone → HCID 178443326, compound

HRID 1437082Notes

Reaction equation

HRID 1437082 reaction equation
CO.Cl.Cl.Cl.[CH2:6]([NH:13][C:14]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[NH:18])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH3:35][C:36]([CH3:38])=O>>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH3:35][C:36]1([CH3:38])[N:15]=[C:14]([NH:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[N:18]1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 971Oxalic AcidHCID 178443503HCID 178443503, compound

Product 1

HCID 178443326HCID 178443326, compound

Procedure

140 ml of methanol, 100 ml of acetone and 0.5 ml of concentrated hydrochloric acid were added to 8.0 g (19.1 mmol) of N1-benzyl-N5-nonyl-biguanide dihydrochloride. The mixture was refluxed for 20 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 100 ml of ethanol, and to the solution were added 60 ml of water and 8.4 ml of 5N aqueous sodium hydroxide. The mixture was refluxed for 1.5 hours, concentrated under reduced pressure, and extracted with ethyl acetate. The extract was washed with water, and the solvent was distilled off under reduced pressure. The residue was dissolved in 50 ml of 70% aqueous acetonitrile, and to the solution was added 4.8 g (38.2 mmol) of oxalic acid dehydrate. The mixture was dissolved under heating, and then cooled. The resulting crystals were recrystallized from 70% aqueous acetonitrile to obtain 8.1 g of colorless crystals having a melting point of 105 to 107° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of ethanol
  4. additionto the solution were added 60 ml of water and 8.4 ml of 5N aqueous sodium hydroxide
  5. temperatureThe mixture was refluxed for 1.5 hours
  6. concentrationconcentrated under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. distillationthe solvent was distilled off under reduced pressure
  10. dissolutionThe residue was dissolved in 50 ml of 70% aqueous acetonitrile
  11. dissolutionThe mixture was dissolved
  12. temperatureunder heating
  13. temperaturecooled
  14. customThe resulting crystals were recrystallized from 70% aqueous acetonitrile

Sources & evidence

ORD record
ord-63fa6dfaf6ff44f48f2cd5237ed50dec
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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