Acetone → HCID 178476238, compound

HRID 1437091Notes

Reaction equation

HRID 1437091 reaction equation
C[OH:2].Cl.Cl.Cl.[CH:6]1([CH2:12][NH:13][C:14]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[NH:18])=[NH:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:28][C:29]([CH3:31])=[O:30]>>[C:29]([OH:2])(=[O:30])[CH3:31].[CH2:20]([NH:19][C:17]1[NH:16][C:14]([NH:13][CH2:12][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)=[N:15][C:29]([CH3:31])([CH3:28])[N:18]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443630HCID 178443630, compound

Product 1

HCID 178476238HCID 178476238, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.6 ml of concentrated hydrochloric acid were added to 9.0 g (23.5 mmol) of N1-cyclohexylmethyl-N5-octyl-biguanide dihydrochloride. The mixture was refluxed for 21 hours, and the solvent was distilled off under reduced pressure. To the residue were added 120 ml of ethanol, 80 ml of water, and 9.5 ml of 5N sodium hydroxide, and the mixture was refluxed for 1 hour, concentrated under reduced pressure, and extracted with methyl ethyl ketone. The extract was washed with water, and 1.7 g of acetic acid was added thereto. The solvent was distilled of f under reduced pressure, and the residue was dried well, and recrystallized from methyl ethyl ketone two times to obtain 4.9 g of colorless crystals having a melting point of 70 to 73° C.

Workup

  1. temperatureThe mixture was refluxed for 21 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 120 ml of ethanol, 80 ml of water, and 9.5 ml of 5N sodium hydroxide
  4. temperaturethe mixture was refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with methyl ethyl ketone
  7. washThe extract was washed with water, and 1.7 g of acetic acid
  8. additionwas added
  9. distillationThe solvent was distilled of f under reduced pressure
  10. customthe residue was dried well
  11. customrecrystallized from methyl ethyl ketone two times

Sources & evidence

ORD record
ord-75c03453004a49b5bb6796452fa075fc
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

Loading…