Acetone → HCID 178443233, compound

HRID 1437101Notes

Reaction equation

HRID 1437101 reaction equation
CO.Cl.Cl.Cl.[S:6]([C:10]1[CH:35]=[CH:34][C:13]([CH2:14][NH:15][C:16]([NH:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[NH:20])=[NH:17])=[CH:12][CH:11]=1)(=[O:9])(=[O:8])[NH2:7].[CH3:36][C:37]([CH3:39])=O>>[CH3:36][C:37]1([CH3:39])[N:17]=[C:16]([NH:15][CH2:14][C:13]2[CH:12]=[CH:11][C:10]([S:6](=[O:8])(=[O:9])[NH2:7])=[CH:35][CH:34]=2)[NH:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N:20]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443251HCID 178443251, compound

Product 1

HCID 178443233HCID 178443233, compound

Procedure

100 ml of methanol, 80 ml of acetone and 0.3 ml of concentrated hydrochloric acid were added to 5.5 g (10.0 mmol) of N1-(4-sulfamoylbenzyl)-N5-dodecyl-biguanide dihydrochloride. The mixture was refluxed for 22 hours, and the solvent was distilled off under reduced pressure. To the residue were added 60 ml of ethanol, 40 ml of water and 6.2 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 repeatedly from a mixture of methyl ethyl ketone and ethanol (8:2) and then from ethanol to obtain 1.4 g of colorless crystals having a melting point of 188 to 191° C.

Workup

  1. temperatureThe mixture was refluxed for 22 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 60 ml of ethanol, 40 ml of water and 6.2 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 repeatedly from a mixture of methyl ethyl ketone and ethanol (8:2)

Sources & evidence

ORD record
ord-5127e21bc10a44218bd30143f925f07b
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

Loading…