Acetone → HCID 178476243, compound

HRID 1437094Notes

Reaction equation

HRID 1437094 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][CH3:26])=[NH:19])=[NH:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:27][C:28]([CH3:30])=[O:29]>>[C:28]([OH:2])(=[O:29])[CH3:30].[CH2:6]([NH:14][C:15]1[NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:19][C:28]([CH3:30])([CH3:27])[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 178443640HCID 178443640, compound

Product 1

HCID 178476243HCID 178476243, compound

Procedure

120 ml of methanol, 100 ml of acetone and 0.7 ml of concentrated hydrochloric acid were added to 10.0 g (27.0 mmol) of N1-octyl-N5-hexyl-biguanide dihydrochloride. The mixture was refluxed for 40 hours, and the solvent was distilled off under reduced pressure. To half amount of the residue were added 70 ml of ethanol, 46 ml of water and 6 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 the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone to obtain 3.7 g of colorless crystals having a melting point of 92 to 94° C.

Workup

  1. temperatureThe mixture was refluxed for 40 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo half amount of the residue were added 70 ml of ethanol, 46 ml of water and 6 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
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-1acee1deb1594f11a8c27a9d2dc5b524
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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