Acetone → HCID 178476237, compound

HRID 1437083Notes

Reaction equation

HRID 1437083 reaction equation
C[OH:2].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][CH3:27])=[NH:18])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:28][C:29]([CH3:31])=[O:30]>>[C:29]([OH:2])(=[O:30])[CH3:31].[CH3:28][C:29]1([CH3:31])[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][CH3:27])=[N:18]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443629HCID 178443629, compound

Product 1

HCID 178476237HCID 178476237, compound

Procedure

100 ml of methanol, 100 ml of acetone and 0.4 ml of concentrated hydrochloric acid were added to 5.0 g (13.3 mmol) of N1-benzyl-N5-octyl-biguanide dihydrochloride. The mixture was refluxed for 22 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 80 ml of water and 5.8 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, and a portion (2.8 g) of 5.8 g of the resulting crystals were recrystallized from ether to obtain 1.1 g of colorless crystals having a melting point of 88 to 91° C.

Workup

  1. temperatureThe mixture was refluxed for 22 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 80 ml of water and 5.8 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. customa portion (2.8 g) of 5.8 g of the resulting crystals were recrystallized from ether

Sources & evidence

ORD record
ord-45ff978155d04914bb907262677103d7
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

Loading…