Triethylamine → 4-[3-(4-n-Butoxybenzoylamino)propylthio]pyridine hydrochloride

HRID 274652

Reaction equation

HRID 274652 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.[CH2:21]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([Cl:32])=[O:31])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[ClH:32].[CH2:21]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([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:31])=[CH:33][CH:34]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190791454-[3-(4-n-Butoxybenzoylamino)propylthio]pyridine hydrochlorideYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 0.94 ml (4.96 mmol) of 4-n-butoxybenzoyl 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 1.10 g of the desired compound (free base). (76.9%,.colorless-powder), mp: 98.0°-99.0° 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)

Sources & evidence

ORD record
ord-7b9897f84c274d8ca8cd4625475b187d
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Linked notes

Loading…