Triethylamine → 4-[3-(N-dodecylamino)propylthio]pyridine

HRID 6145

Reaction equation

HRID 6145 reaction equation
O[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:24]([NH2:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C(Cl)Cl>[CH2:24]([NH:36][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13583DodecylamineHCID 31297Methanesulfonyl chlorideHCID 190791344-(3-Hydroxypropylthio)pyridine

Product 1

HCID 190792524-[3-(N-dodecylamino)propylthio]pyridineYield 29.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 120 ml of methylene chloride was dissolved 5.60 g (33.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.53 ml (39.7 mmol) of triethylamine. 3.07 ml (39.7 mmol) of methanesulfonyl chloride was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. 5.34 g (28.8 mmol) of dodecylamine was added to 7.12 g of the residue, and the mixture was heated at 80° C. for 3 hours. After cooling, the mixture was purified by column chromatography (eluent: chloroform/methanol=25:1) to obtain 2.86 g of the desired compound (yield: 29.5%, yellow oil).

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  2. customdried
  3. distillationthe solvent was distilled off
  4. temperaturethe mixture was heated at 80° C. for 3 hours
  5. temperatureAfter cooling
  6. customthe mixture was purified by column chromatography (eluent: chloroform/methanol=25:1)

Sources & evidence

ORD record
ord-e49129c86d4242ec88a7e0cdf427a563
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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