Hydrochloric Acid → HCID 178476232, compound

HRID 1437075Notes

Reaction equation

HRID 1437075 reaction equation
[CH3:1][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.[OH-].[Na+].[CH2:32]([OH:34])[CH3:33]>O.CC(C)=O>[C:32]([OH:2])(=[O:34])[CH3:33].[CH3:1][C:32]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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 887MethanolHCID 14798Sodium HydroxideHCID 178443402HCID 178443402, compound

Product 1

HCID 178476232HCID 178476232, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

140 ml of methanol, 100 ml of acetone and 0.6 ml of concentrated hydrochloric acid were added to 8.5 g (21.0 mmol) of N1-benzyl-N5-decyl-biguanide dihydrochloride, and the mixture was refluxed for 24 hours. The solvent was distilled off under reduced pressure to give a residue, which was dissolved in 150 ml of ethanol. To the solution were added 100 ml of water and 10 ml of 5N aqueous sodium hydroxide, and the mixture was refluxed for 1.5 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water, concentrated under reduced pressure to remove the solvent, and dried well under reduced pressure to obtain 8 g of a colorless solid (1). Then, 3.6 g (9.6 mmol) of the solid was dissolved in 30 ml of 70% aqueous acetonitrile, and to the solution was added 16 g (15.4 mmol) of malonic acid. The mixture was dissolved under heating, and then cooled. The resulting crystals were recrystallized from 70% aqueous acetonitrile to obtain 3.9 g of colorless crystals (2) having a melting point of 78 to 81° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customto give a residue, which
  4. temperaturethe mixture was refluxed for 1.5 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customdried well under reduced pressure

Sources & evidence

ORD record
ord-cd3505527e0549029cad77ae5cdfcd3c
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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