Hydrochloric Acid → HCID 69054656, compound

HRID 1437062Notes

Reaction equation

HRID 1437062 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[ClH:11].Cl.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]([NH2:29])=[NH:28])=[NH:25])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)C>[ClH:11].[CH2:2]([CH:1]1[N:23]([C:20]2[CH:21]=[CH:22][C:17]([C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:18][CH:19]=2)[C:24]([NH2:25])=[N:26][C:27]([NH2:29])=[N:28]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31289NonanalHCID 178441022HCID 178441022, compound

Product 1

HCID 69054656HCID 69054656, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 ml of ethanol, 4.8 ml (27.9 mmol) of 1-nonanal and 0.8 ml of concentrated hydrochloric acid were added to 5.0 g (18.5 mmol) of N1-(4-tert-butylphenyl)-biguanide hydrochloride, and the mixture was refluxed for 15 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 recrystallized from 70% aqueous acetonitrile to obtain 16 g of colorless crystals having a melting point of 231 to 234° C.

Workup

  1. temperaturethe mixture was refluxed for 15 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)), and
  6. customrecrystallized from 70% aqueous acetonitrile

Sources & evidence

ORD record
ord-d5d15e60504642bb958453f2ef7b1d51
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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