Dodecanoyl chloride → 4-[3-(Lauroylamino)propylthio]pyridine

HRID 964066Notes

Reaction equation

HRID 964066 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[C:21]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 152952594-[3-(Lauroylamino)propylthio]pyridineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 1.15 ml (4.96 mmol) of lauroyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for. 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with hexane and dried to obtain 1.05 g of the desired compound (72.2%, colorless powder), mp: 71.0°-72.0° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for
  3. custom30 minutes
  4. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  8. customto obtain the powder which
  9. washwas washed with hexane
  10. customdried

Sources & evidence

ORD record
ord-861ddfc2462048649f82f00e83e87bf2
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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