Acetone → HCID 178476249, compound

HRID 1437096Notes

Reaction equation

HRID 1437096 reaction equation
C[OH:2].Cl.Cl.Cl.[CH2:6]([NH:12][C:13]([NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[NH:17])=[NH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:26][C:27]([CH3:29])=[O:28]>>[C:27]([OH:2])(=[O:28])[CH3:29].[CH3:26][C:27]1([CH3:29])[N:14]=[C:13]([NH:12][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[N:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443991HCID 178443991, compound

Product 1

HCID 178476249HCID 178476249, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.7 ml of concentrated hydrochloric acid were added to 10.0 g (28.1 mmol) of N1-hexyl-N5-heptyl-biguanide dihydrochloride. The mixture was refluxed for 23 hours, and the solvent was distilled off under reduced pressure. To the residue were added 100 ml of ethanol, 60 ml of water and 11.3 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 successively with 10% aqueous sodium acetate and water, and the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone to obtain 8.4 g of colorless crystals having a melting point of 70 to 75° C.

Workup

  1. temperatureThe mixture was refluxed for 23 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 11.3 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 successively with 10% aqueous sodium acetate and water
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-4b225dc4445541e1bc235c4721fd1180
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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