Acetone → HCID 178476239, compound

HRID 1437087Notes

Reaction equation

HRID 1437087 reaction equation
C[OH:2].Cl.Cl.Cl.[CH3:6][C:7]1[CH:28]=[CH:27][C:10]([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][CH3:26])=[NH:17])=[NH:14])=[CH:9][CH:8]=1.[CH3:29][C:30]([CH3:32])=[O:31]>>[C:30]([OH:2])(=[O:31])[CH3:32].[CH2:19]([NH:18][C:16]1[NH:15][C:13]([NH:12][CH2:11][C:10]2[CH:9]=[CH:8][C:7]([CH3:6])=[CH:28][CH:27]=2)=[N:14][C:30]([CH3:32])([CH3:29])[N:17]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443631HCID 178443631, compound

Product 1

HCID 178476239HCID 178476239, compound

Procedure

300 ml of methanol, 180 ml of acetone and 1.2 ml of concentrated hydrochloric acid were added to 18.0 g (46.1 mmol) of N1-4-methylbenzyl-N5-octyl-biguanide dihydrochloride. The mixture was refluxed for 24 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 200 ml of ethanol, and to the solution were added 140 ml of water and 18.5 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 ether, and cooled. The resulting precipitated crystals were filtered off, and recrystallized from ethanol/ether to obtain 10.1 g of colorless crystals having a melting point of 101 to 102° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 200 ml of ethanol
  4. additionto the solution were added 140 ml of water and 18.5 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 ether
  11. temperaturecooled
  12. customThe resulting precipitated crystals
  13. filtrationwere filtered off
  14. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-b668a00fb1d8409fb21c6bfc707aef5a
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

Loading…