Acetone → HCID 15512739, compound

HRID 1976516Notes

Reaction equation

HRID 1976516 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[C:5]#[N:6].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:27](=[O:30])([O-])[O-].[K+].[K+].[CH3:33][C:34]([CH3:36])=O>O>[CH2:12]([O:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:30][CH2:27][CH2:33][CH2:34][CH2:36][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])[CH:9]=1)[C:5]#[N:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 123941-BromopentadecaneHCID 879523,5-Dihydroxybenzonitrile

Product 1

HCID 15512739HCID 15512739, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-dihydroxybenzonitrile (0.50 g), 1-bromopentadecane (2.70 g), potassium carbonate (2.56 g), and 30 ml of acetone were mixed and the mixture was heated overnight under reflux. After water was added, the mixture was extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain 0.33 g of 3,5-dipentadecyloxybenzonitrile as colorless crystals. This product was dissolved in a mixed solvent of 20 ml of methanol and 35 ml of benzene and hydrogen chloride gas was allowed to flow into the mixture for 1 hour under ice-cooling. The solvent was removed by evaporation under reduced pressure and the thus-obtained crystals were recrystallized from chloroform and hexane to obtain 0.28 g of 3,5-dipentadecyloxy-α-methoxy-α-iminotoluene hydrochloride. This product was dissolved in 10 ml of chloroform, ammonia gas was allowed to flow into the solution for 40 minutes under ice-cooling, then the mixture was heated for 4.5 hours under reflux. After the solvent was removed by evaporation under reduced pressure, the materials insoluble in chloroform were removed from the resulting solid to obtain 0.20 g of 3,5-dipentadecyloxybenzamidine as colorless crystals. The data obtained by instrumental analysis of this compound support the structure represented by the following formula 3.

Workup

  1. temperaturethe mixture was heated overnight
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-97ec092f65904b6a874d4106d40a70ff
Source dataset
uspto-grants-2001_05
Patent number
US06228391B1

Reaction notes

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