Acetone → HCID 178476231, compound

HRID 1437098Notes

Reaction equation

HRID 1437098 reaction equation
C[OH:2].Cl.Cl.[CH2:5]([NH:7][C:8]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[NH:12])=[NH:9])[CH3:6].[CH3:26][C:27]([CH3:29])=[O:28]>>[C:27]([OH:2])(=[O:28])[CH3:29].[CH2:5]([NH:7][C:8]1[NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[N:12][C:27]([CH3:29])([CH3:26])[N:9]=1)[CH3:6]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443252HCID 178443252, compound

Product 1

HCID 178476231HCID 178476231, compound

Procedure

100 ml of methanol, 80ml of acetone and 2.6 ml of concentrated hydrochloric acid were added to 8.0 g (24.0 mmol) of N1-ethyl-N5-dodecyl-biguanide hydrochloride, and the mixture was refluxed for 64 hours. The solvent was distilled off under reduced pressure. To the residue were added 100 ml of ethanol, 60 ml of water and 12.0 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 successively with 10% aqueous sodium acetate and water, and the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone to obtain 6.2 g of colorless crystals having a melting point of 79 to 82° 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 100 ml of ethanol, 60 ml of water and 12.0 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 successively with 10% aqueous sodium acetate and water
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-d410b55e2a184e46921f9d87eb423849
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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