Hydrochloric Acid → HCID 69063241, compound

HRID 1437064Notes

Reaction equation

HRID 1437064 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[ClH:11].Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:16]=1[NH:25][C:26]([NH:28][C:29]([NH2:31])=[NH:30])=[NH:27]>C(O)C>[ClH:11].[CH2:2]([CH:1]1[N:25]([C:16]2[CH:17]=[C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])[CH:19]=[CH:20][C:15]=2[O:14][CH3:13])[C:26]([NH2:27])=[N:28][C:29]([NH2:31])=[N:30]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31289NonanalHCID 178490080HCID 178490080, compound

Product 1

HCID 69063241HCID 69063241, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 ml of ethanol, 3.7 g (26.2 mmol) of 1-nonanal and 0.8 ml of concentrated hydrochloric acid were added to 6.0 g (20.0 mmol) of N1-(2-methoxy-5-tert-butylphenyl)-biguanide hydrochloride, and the mixture was refluxed for 20 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)). The eluate was dissolved in 80% aqueous ethanol, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol and ether to obtain 2.3 g of pale yellow crystals having a melting point of 217 to 219° C.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (
  4. washelution
  5. additionwith a mixture of chloroform and methanol (9:1.5))
  6. dissolutionThe eluate was dissolved in 80% aqueous ethanol
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethanol and ether

Sources & evidence

ORD record
ord-e912bcd772734e299d436e31486a7438
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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