Triethylamine → 4-[3-(4-Methylbenzoylamino)propylthio]pyridine

HRID 6106

Reaction equation

HRID 6106 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]1([CH3:30])[CH:26]=[CH:25][C:24]([C:27](Cl)=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:30][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:28])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190792124-[3-(4-Methylbenzoylamino)propylthio]pyridineYield 76.6%

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 0.65 ml (4.96 mmol) of 4-toluoyl 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 ether and dried to obtain 910 mg of the desired compound (76.6%, colorless powder), mp: 110.0°-111.0° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  7. customto obtain the powder which
  8. washwas washed with ether
  9. customdried

Sources & evidence

ORD record
ord-f9fba7e62cfc4f3dacab24daff205a17
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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