Acetone → HCID 178476246, compound

HRID 1437088Notes

Reaction equation

HRID 1437088 reaction equation
C[OH:2].Cl.Cl.Cl.[CH3:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][NH:12][C:13]([NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[NH:17])=[NH:14])=[CH:9][CH:8]=1.[CH3:28][C:29]([CH3:31])=[O:30]>>[C:29]([OH:2])(=[O:30])[CH3:31].[CH3:28][C:29]1([CH3:31])[N:14]=[C:13]([NH:12][CH2:11][C:10]2[CH:9]=[CH:8][C:7]([CH3:6])=[CH:27][CH:26]=2)[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[N:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443988HCID 178443988, compound

Product 1

HCID 178476246HCID 178476246, compound

Procedure

140 ml of methanol, 60 ml of acetone and 0.7 ml of concentrated hydrochloric acid were added to 10.0 g (26.6 mmol) of N1-4-methylbenzyl-N5-heptyl-biguanide dihydrochloride. The mixture was refluxed for 24 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 100 ml of ethanol, and to the solution were added 60 ml of water and 10.8 ml of 5N aqueous sodium hydroxide. 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 solution, and washed with water. The solvent was distilled off under reduced pressure, and the residue was recrystallized from methyl ethyl ketone to obtain 7.2 g of colorless crystals having a melting point of 102 to 104° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of ethanol
  4. additionto the solution were added 60 ml of water and 10.8 ml of 5N aqueous sodium hydroxide
  5. temperatureThe mixture was refluxed for 1 hour
  6. concentrationconcentrated under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with 10% aqueous sodium acetate solution
  9. washwashed with water
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-a425a47ed1a54f82a9b97303668a0d7e
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

Loading…