Acetone → HCID 178476240, compound

HRID 1437086Notes

Reaction equation

HRID 1437086 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][CH2:27][CH3:28])=[NH:19])=[NH:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:29][C:30]([CH3:32])=[O:31]>>[C:30]([OH:2])(=[O:31])[CH3:32].[CH2:21]([NH:20][C:18]1[NH:17][C:15]([NH:14][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:16][C:30]([CH3:32])([CH3:29])[N:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443637HCID 178443637, compound

Product 1

HCID 178476240HCID 178476240, compound

Procedure

150 ml of methanol, 150 ml of acetone and 0.8 ml of concentrated hydrochloric acid were added to 13.1 g (33.6 mmol) of N1-phenethyl-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 150 ml of ethanol, and to the solution were added 100 ml of water and 13 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 recrystallized two times from ethanol/ether to obtain 4.8 g of colorless crystals having a melting point of 86 to 88° 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 150 ml of ethanol
  4. additionto the solution were added 100 ml of water and 13 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. customThe residue was recrystallized two times from ethanol/ether

Sources & evidence

ORD record
ord-b5606ff42eb24aca8d46fbd226b5a0b3
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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