Hydrochloric Acid → HCID 69059173, compound

HRID 1437099Notes

Reaction equation

HRID 1437099 reaction equation
[CH3:1][O:2][CH2:3][O:4]C.Cl.Cl.Cl.[CH2:9]([NH:17][C:18]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[NH:22])=[NH:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(O)CCC>[C:3]([OH:4])(=[O:2])[CH3:9].[CH2:24]([NH:23][C:21]1[NH:20][C:18]([NH:17][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:19][CH2:1][N:22]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8020DimethoxymethaneHCID 178443638HCID 178443638, compound

Product 1

HCID 69059173HCID 69059173, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

200 ml of butanol, 13 ml (0.15 mol) of methylal and 1.2 ml of concentrated hydrochloric acid were added to 5.8 g (14.6 mmol) of N1,N5-dioctyl-biguanide dihydrochloride, and the mixture was refluxed for 28 hours. The solvent was distilled off under reduced pressure. To the residue were added 50 ml of ethanol, 30 ml of water, and 5.9 ml of 5N sodium hydroxide, and the mixture was refluxed for 1 hour, concentrated under reduced pressure, and extracted with ethyl acetate. The extract was washed successively with 10% aqueous sodium acetate andwater, and the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone to obtain 2.1 g of colorless crystals having a melting point of 117 to 121° C.

Workup

  1. temperaturethe mixture was refluxed for 28 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 50 ml of ethanol, 30 ml of water, and 5.9 ml of 5N sodium hydroxide
  4. temperaturethe mixture was refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed successively with 10% aqueous sodium acetate andwater
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-068b9ef3602143fba7f82ac915d6b7ff
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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