Acetaldehyde → HCID 178443332, compound

HRID 1437053Notes

Reaction equation

HRID 1437053 reaction equation
[CH:1](=O)[CH3:2].[ClH:4].Cl.Cl.[CH3:7][O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[NH:19])=[NH:16])=[CH:11][CH:10]=1>C(O)C>[ClH:4].[CH2:21]([NH:20][CH:18]1[N:19]=[C:1]([CH3:2])[N:16]=[C:15]([NH:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:33][CH:32]=2)[NH:17]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 178443336HCID 178443336, compound

Product 1

HCID 178443332HCID 178443332, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under ice-cooling, 100 ml of ethanol, 5 ml (89.2 mmol) of acetaldehyde and 0.4 ml of concentrated hydrochloric acid were added to 4.0 g (8.9 mmol) of N1-(4-methoxybenzyl)-N5-undecyl-biguanide dihydrochloride, and the mixture was refluxed for 24 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1.5)), and dissolved in 70% aqueous acetonitrile. The solvent was distilled off under reduced pressure, followed by sufficient drying under reduced pressure to obtain 1.4 g of a colorless resinous solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturethe mixture was refluxed for 24 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (
  5. washelution
  6. additionwith a mixture of chloroform and methanol (9:1.5)), and
  7. dissolutiondissolved in 70% aqueous acetonitrile
  8. distillationThe solvent was distilled off under reduced pressure
  9. customby sufficient drying under reduced pressure

Sources & evidence

ORD record
ord-61a40663b2b7453191d53a5eb2b06de9
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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