Hexadecylamine → 5-Amino-2-hexadecylsulfamoyl-1-naphthol

HRID 2198549

Reaction equation

HRID 2198549 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 202399035-Amino-2-hexadecylsulfamoyl-1-naphtholYield 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-acetamino-naphthalene-2-sulfonyl chloride synthesized above in 150 ml of acetone while stirring, and, after completion of the addition, stirring was continued for about one hour at about 40° C. Then, the reaction solution was ice-cooled, 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 NaOH, 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. temperaturecooled
  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 NaOH, 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-025be907829a49caa92065a67490772f
Source dataset
uspto-grants-1982_11
Patent number
US04358532

Linked notes

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