Acetone → HCID 178443328, compound

HRID 1437051Notes

Reaction equation

HRID 1437051 reaction equation
CO.[ClH:3].Cl.Cl.[OH:6][C:7]1[CH:31]=[CH:30][C:10]([CH2:11][NH:12][C:13]([NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[NH:17])=[NH:14])=[CH:9][CH:8]=1.[CH3:32][C:33]([CH3:35])=O>>[ClH:3].[CH2:19]([NH:18][C:16]1[NH:15][C:13]([NH:12][CH2:11][C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:31][CH:30]=2)=[N:14][C:33]([CH3:35])([CH3:32])[N:17]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443334HCID 178443334, compound

Product 1

HCID 178443328HCID 178443328, compound

Procedure

25 ml of methanol, 40 ml of acetone and 0.1 ml of concentrated hydrochloric acid were added to 2.0 g (4.5 mmol) of N1-(4-hydroxybenzyl)-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 (8:1.5)), and then recrystallized with 80% aqueous acetonitrile to obtain 0.73 g of colorless crystals having a melting point of 110 to 112° C.

Workup

  1. temperaturethe mixture was refluxed for 24 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 (8:1.5)), and
  6. customthen recrystallized with 80% aqueous acetonitrile

Sources & evidence

ORD record
ord-e9becc1966a64634b90db94500ec3c91
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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