Acetone → HCID 178476247, compound

HRID 1437097Notes

Reaction equation

HRID 1437097 reaction equation
C[OH:2].Cl.Cl.[CH2:5]([NH:12][C:13]([NH:15][C:16]([NH:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[NH:17])=[NH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:27][C:28]([CH3:30])=[O:29]>>[C:28]([OH:2])(=[O:29])[CH3:30].[CH3:27][C:28]1([CH3:30])[N:17]=[C:16]([NH:18][C:19]([CH3:25])([CH3:26])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[NH:15][C:13]([NH:12][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[N:14]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 887MethanolHCID 178443989HCID 178443989, compound

Product 1

HCID 178476247HCID 178476247, compound

Procedure

100 ml of methanol, 80 ml of acetone and 2.9 ml of concentrated hydrochloric acid were added to 9.0 g (25.9 mmol) of N1-heptyl-N5- (1,1,3,3-tetramethylbutyl)-biguanide hydrochloride. The mixture was refluxed for 21 hours, and the solvent was distilled off under reduced pressure. To the residue were added 100 ml of ethanol, 60 ml of water and 10.6 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 and water, and the solvent was distilled off under reduced pressure. The residue was recrystallized from methyl ethyl ketone two times to obtain 8.3 g of colorless crystals having a melting point of 98 to 101° C.

Workup

  1. temperatureThe mixture was refluxed for 21 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 100 ml of ethanol, 60 ml of water and 10.6 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 and water
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from methyl ethyl ketone two times

Sources & evidence

ORD record
ord-ca9f37f2bb284e78872987e8c4c335bf
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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