Acetone → HCID 178476234, compound

HRID 1437080Notes

Reaction equation

HRID 1437080 reaction equation
C[OH:2].Cl.Cl.Cl.[CH2:6]([NH:13][C:14]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[NH:18])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:29][C:30]([CH3:32])=[O:31]>>[C:30]([OH:2])(=[O:31])[CH3:32].[CH3:29][C:30]1([CH3:32])[N:15]=[C:14]([NH:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[N:18]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443503HCID 178443503, compound

Product 1

HCID 178476234HCID 178476234, compound

Procedure

300 ml of methanol, 250 ml of acetone and 1.2 ml of concentrated hydrochloric acid were added to 18.2 g (46.6 mmol) of N1-benzyl-N5-nonyl-biguanide dihydrochloride. The mixture was refluxed for 22 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 300 ml of ethanol, and to the solution were added 200 ml of water and 18 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 to obtain 18.9 g of colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 22 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 300 ml of ethanol
  4. additionto the solution were added 200 ml of water and 18 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

Sources & evidence

ORD record
ord-26dc260cb24c4f6c93f8a2520e49aea9
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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