Acetone → HCID 178476241, compound

HRID 1437092Notes

Reaction equation

HRID 1437092 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][CH3:28])=[NH:19])=[NH:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:29][C:30]([CH3:32])=[O:31]>>[C:30]([OH:2])(=[O:31])[CH3:32].[CH2:21]([NH:20][C:18]1[NH:17][C:15]([NH:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:16][C:30]([CH3:32])([CH3:29])[N:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443638HCID 178443638, compound

Product 1

HCID 178476241HCID 178476241, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.6 ml of concentrated hydrochloric acid were added to 10.0 g (25.1 mmol) of N1,N5-dioctyl-biguanide dihydrochloride. The mixture was refluxed for 64 hours, and the solvent was distilled off under reduced pressure. To the residue were added 110 ml of ethanol, 60 ml of water and 10.1 ml of 5N sodium hydroxide, and the mixture was refluxed for 1 hour, concentrated under reduced pressure, and then extracted with ethyl acetate. The extract was washed with water, and the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone to obtain 7.2 g of colorless crystals having a melting point of 91 to 93° C.

Workup

  1. temperatureThe mixture was refluxed for 64 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 110 ml of ethanol, 60 ml of water and 10.1 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 water
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-cfa6407a15e245dea916c28c334d6568
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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