2-Thiophenecarboxylic acid → 4-[3-(5-Methylthenoylamino)propylthio]pyridine

HRID 2210133Notes

Reaction equation

HRID 2210133 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.ON1C(=O)CC[C:11]1=O.Cl.C(N=C=NCCCN(C)C)C.[NH2:29][CH2:30][CH2:31][CH2:32][S:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:11][C:5]1[S:1][C:2]([C:6]([NH:29][CH2:30][CH2:31][CH2:32][S:33][C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[O:8])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 152276954-(3-Aminopropylthio)pyridine

Product 1

HCID 190792384-[3-(5-Methylthenoylamino)propylthio]pyridineYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.27 g (8.91 mmol) of 5-methyl-2=thiophenecarboxylic 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 1.68 g of the desired compound (yield: 64.5% colorless powder)

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. washThe reaction mixture was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  8. customto obtain powder
  9. customThe powder thus obtained
  10. washwas washed with ether
  11. customdried

Sources & evidence

ORD record
ord-19c3d6da40724b6e9708c8003ded70b4
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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