Acetone → HCID 178476242, compound

HRID 1437093Notes

Reaction equation

HRID 1437093 reaction equation
C[OH:2].Cl.Cl.Cl.[CH2:6]([NH:14][C:15]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[NH:19])=[NH:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:28][C:29]([CH3:31])=[O:30]>>[C:29]([OH:2])(=[O:30])[CH3:31].[CH2:6]([NH:14][C:15]1[NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N:19][C:29]([CH3:31])([CH3:28])[N:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443639HCID 178443639, compound

Product 1

HCID 178476242HCID 178476242, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.5 ml of concentrated hydrochloric acid were added to 8.0 g (20.8 mmol) of N1-octyl-N5-heptyl-biguanide dihydrochloride. The mixture was refluxed for 64 hours, and the solvent was distilled off under reduced pressure. To the residue were added 100 ml of ethanol, 60 ml of water and 8.5 ml of 5N sodium hydroxide, and the mixture was refluxed for 1 hour, concentrated under reduced pressure, and extracted with ethyl acetate. The extract was washed with water, and 1.3 g of acetic acid was added thereto. The solvent was distilled off under reduced pressure, and the residue was dried well, and recrystallized from methyl ethyl ketone to obtain 4.1 g of colorless crystals having a melting point of 82 to 84° C.

Workup

  1. temperatureThe mixture was refluxed for 64 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 100 ml of ethanol, 60 ml of water and 8.5 ml of 5N sodium hydroxide
  4. temperaturethe mixture was refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water, and 1.3 g of acetic acid
  8. additionwas added
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was dried well
  11. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-2fd32c5433b643abaadc6bc64076098b
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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