Acetone → HCID 178476248, compound

HRID 1437095Notes

Reaction equation

HRID 1437095 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][CH3:26])=[NH:18])=[NH:15])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:27][C:28]([CH3:30])=[O:29]>>[C:28]([OH:2])(=[O:29])[CH3:30].[CH2:20]([NH:19][C:17]1[NH:16][C:14]([NH:13][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[N:15][C:28]([CH3:30])([CH3:27])[N:18]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443990HCID 178443990, compound

Product 1

HCID 178476248HCID 178476248, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.7 ml of concentrated hydrochloric acid were added to 10.0 g (27.0 mmol) of N1,N5-diheptyl-biguanide dihydrochloride, and the mixture was refluxed for 24 hours. The solvent was distilled off under reduced pressure. To the residue were added 100 ml of ethanol, 60 ml of water, and 10.9 ml of 5N sodium hydroxide, and the mixture was refluxed for 1 hour, concentrated under reduced pressure, and extracted with ethyl acetate. The extract was washed with 10% aqueous sodium acetate, washed with water, and concentrated under reduced pressure to remove the solvent. The residue was recrystallized from methyl ethyl ketone to obtain 7.3 g of colorless crystals having a melting point of 83 to 85° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 100 ml of ethanol, 60 ml of water, and 10.9 ml of 5N sodium hydroxide
  4. temperaturethe mixture was refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with 10% aqueous sodium acetate
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure
  10. customto remove the solvent
  11. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-2139c5669a704c598907a7ff1def89aa
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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