Acetone → HCID 178476232, compound

HRID 1437081Notes

Reaction equation

HRID 1437081 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][CH2:28][CH3:29])=[NH:18])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=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: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][CH2:28][CH3:29])=[N:18]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443402HCID 178443402, compound

Product 1

HCID 178476232HCID 178476232, compound

Procedure

110 ml of methanol, 80ml of acetone and 0.5 ml of concentrated hydrochloric acid were added to 6.8 g (16.9 mmol) of N1-benzyl-N5-decyl-biguanide dihydrochloride. The mixture was refluxed for 22 hours, and the solvent was distilled off under reduced pressure, and the residue was dissolved in 100 ml of ethanol. To the solution were added 80 ml of water and 7 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 from ethanol/ether to obtain 2.9 g of colorless crystals having a melting point of 106 to 108° C.

Workup

  1. temperatureThe mixture was refluxed for 22 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 100 ml of ethanol
  4. additionTo the solution were added 80 ml of water and 7 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 from ethanol/ether

Sources & evidence

ORD record
ord-b9591d2b59bc47de84bfa0416d40c1aa
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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