Triethylamine → 4-[3-(3-Methylthenoylamino)propylthio]pyridine
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.[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27](Cl)=[O:28]>C(Cl)Cl>[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27]([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:28]Participants
Procedure
In 100 ml of benzene was suspended 3.00 g (21.1 mmol) of 3-methyl-2-thiophenecarboxylic acid, oxalyl chloride [7.36 ml (84.4 mmol)] was added and the mixture was refluxed for 2 hours. After cooling, the solvent was distilled off to obtain 3.40 g of 3-methylthenoyl chloride (yield: quant.). To a solution of 1.50 g (6.23 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.61 ml (18.7 mmol) of triethylamine in 60 ml of methylene chloride, 1.20 ml (7.48 mmol) of the 3-methylthenoyl chloride was added under ice-cooling with stirring. 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. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain powder. The powder was washed with ether and dried to obtain 1.54 g of the desired compound (yield: 84.5%, pale yellow powder).
Workup
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 30 minutes
- washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
- customdried
- distillationthe solvent was distilled off
- customThe residue was purified by column chromatography (eluent: ethyl acetate)
- customto obtain powder
- washThe powder was washed with ether
- customdried
Sources & evidence
- ORD record
- ord-f56f6d364c6f42abae9c794c891f57f9
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246948
Reaction notes
Loading…