N-Hydroxysuccinimide → 4-[3-(4,5-Dibromothenoylamino)propylthio]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[S:5][C:6]=1[Br:7].ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.[NH2:31][CH2:32][CH2:33][CH2:34][S:35][C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:31][CH2:32][CH2:33][CH2:34][S:35][C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[O:10])[S:5][C:6]=1[Br:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.55 g (8.91 mmol) of 4,5-dibromothiophene-2-carboxylic acid and 1.33 g (11.6 mmol) of N-hydroxysuccinimide in 90 ml of methylene chloride, 2.05 g (10.7 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1 hour. Further, 1.50 g (8.91 mmol) of 4-(3-aminopropylthio)pyridine was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with 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 thus obtained was washed with ether and dried to obtain 2.79 g of the desired compound (yield: 71.8%, colorless powder).
Workup
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 1 hour
- stirringthe mixture was stirred at room temperature for 2 hours
- washThe reaction mixture was washed with water
- customdried
- customThe residue was purified by column chromatography (eluent: ethyl acetate)
- customto obtain powder
- customThe powder thus obtained
- washwas washed with ether
- customdried
Sources & evidence
- ORD record
- ord-4364be282ffe458daa5215a9ec3098d8
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05389658
Reaction notes
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