Hexadecylamine → HCID 20239903, compound

HRID 363974

Reaction equation

HRID 363974 reaction equation
[CH2:1]([NH2:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C([O:21][C:22]1[C:31]2[C:26](=[C:27]([NH:32]C(C)=O)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:36](Cl)(=[O:38])=[O:37])(=O)C>CC(C)=O>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[CH:25]=[CH:24][C:23]([S:36](=[O:38])(=[O:37])[NH:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:22]2[OH:21]

Participants

4

Reactant 2

HCID 8926HexadecylamineHCID 941252-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-

Product 1

HCID 20239903HCID 20239903, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

30 g of hexadecylamine was dissolved in 250 liters of acetone. To this solution was added gradually a solution of 40 g of 1-acetoxy-5-acetaminonaphthalene-2-sulfonyl chloride synthesized above in 150 ml of acetone while stirring, and, after completion of the addition, stirring was continued for about 1 hour at about 40° C. Then, the reaction solution was cooled with ice, and the precipitated crystals were collected by filtration and well washed with 1 liter of methanol. The crystals were refluxed for 8 hours together with 200 ml of ethanol, 30 g of sodium hydroxide and 100 ml of water. After being allowed to cool to room temperature, the solution was neutralized with acetic acid, and the crystals thus precipitated were collected by filtration and recrystallized from an ethanol-water mixture solvent to obtain 22 g (54% yield) of product.

Workup

  1. additionafter completion of the addition
  2. stirringstirring
  3. temperatureThen, the reaction solution was cooled with ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwell washed with 1 liter of methanol
  6. temperatureThe crystals were refluxed for 8 hours together with 200 ml of ethanol, 30 g of sodium hydroxide and 100 ml of water
  7. customthe crystals thus precipitated
  8. filtrationwere collected by filtration
  9. customrecrystallized from an ethanol-water mixture solvent

Sources & evidence

ORD record
ord-cb1a087fe2cd44fb9414def1e3573f40
Source dataset
uspto-grants-1986_08
Patent number
USH0000098

Linked notes

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