Acetone → HCID 178476235, compound

HRID 1437085Notes

Reaction equation

HRID 1437085 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][CH2:28][CH3:29])=[NH:19])=[NH:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:30][C:31]([CH3:33])=[O:32]>>[C:31]([OH:2])(=[O:32])[CH3:33].[CH3:30][C:31]1([CH3:33])[N:16]=[C:15]([NH:14][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:19]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443504HCID 178443504, compound

Product 1

HCID 178476235HCID 178476235, compound

Procedure

350 ml of methanol, 350 ml of acetone and 1.9 ml of concentrated hydrochloric acid were added to 31.0 g (76.7 mmol) of N1-phenethyl-N5-nonyl-biguanide dihydrochloride. The mixture was refluxed for 16 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 350 ml of ethanol, and to the solution were added 250 ml of water and 31 ml of 5N 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 from ether to obtain 16.3 g of colorless crystals having a melting point of 72 to 76° C.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 350 ml of ethanol
  4. additionto the solution were added 250 ml of water and 31 ml of 5N 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 from ether

Sources & evidence

ORD record
ord-93726bc1b713413d80b6d62d10999c7b
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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