Hydrochloric Acid → HCID 69056000, compound

HRID 1437079Notes

Reaction equation

HRID 1437079 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[ClH:15].Cl.[C:17]1([NH:23][C:24]([NH:26][C:27]([NH2:29])=[NH:28])=[NH:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[ClH:15].[CH2:3]([C:2]1([CH3:1])[N:23]([C:17]2[CH:18]=[CH:19][C:20]([Cl:15])=[CH:21][CH:22]=2)[C:24]([NH2:25])=[N:26][C:27]([NH2:29])=[N:28]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 116222-TridecanoneHCID 178479480HCID 178479480, compound

Product 1

HCID 69056000HCID 69056000, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 ml of ethanol, 10.1 g (50.9 mmol) of 2-tridecanone and 2.0 ml of concentrated hydrochloric acid were added to 12.0 g (48.4 mmol) of N1-phenyl-biguanide hydrochloride, and the mixture was refluxed for 40 hours. The solvent was distilled off under reduced pressure, and the residue was purified two times by silica gel column chromatography (elution with a mixture of chloroform and methanol (8:1.5) and subsequently with a mixture of chloroform/methanol/acetic acid (8:0.5:0.5→8:1:1)). The eluate was dissolved in 80% aqueous ethanol, and the solvent was distilled off under reduced pressure. The residue was dried well under reduced pressure to obtain 6.6 g of a pale yellow resinous solid.

Workup

  1. temperaturethe mixture was refluxed for 40 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified two times by silica gel column chromatography (
  4. washelution
  5. additionwith a mixture of chloroform and methanol (8:1.5)
  6. additionsubsequently with a mixture of chloroform/methanol/acetic acid (8:0.5:0.5→8:1:1))
  7. dissolutionThe eluate was dissolved in 80% aqueous ethanol
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was dried well under reduced pressure

Sources & evidence

ORD record
ord-582b7b0099ec4b6fbb38a7f910b875c5
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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