Pyridine → HCID 868244, compound

HRID 1530904Notes

Reaction equation

HRID 1530904 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[CH3:10][O:9][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[NH:1][S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 868244HCID 868244, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5.00 g (0.032 mol) of 3-anino-2-carbomethoxythiophene dissolved in 40 mL of chloroform was added 7.73 mL (0.032 mol) of pyridine followed by 6.57 g (0.032 mol) of p-methoxybenzenesulfonyl chloride. The reaction mixture was stirred at room temperature for 5 h and then washed with 3N HCl and water. The organics were then dried over Na2SO4, filtered and concentrated in vacuo. The resulting cream colored solid was washed with ether and dried in vacuo to provide 6.89 g (66%) of the desired sulfonamide. Electrospray Mass Spec 328.2 (M+H).

Workup

  1. washwashed with 3N HCl and water
  2. dry with materialThe organics were then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe resulting cream colored solid was washed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1d216c39c2bf46a5aa36796d5fcb645f
Source dataset
uspto-grants-2001_03
Patent number
US06197795B1

Reaction notes

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