Pyridine → HCID 799182, compound

HRID 1387695Notes

Reaction equation

HRID 1387695 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8635Methyl Anthranilate

Product 1

HCID 799182HCID 799182, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g (0.013 mol) of methyl anthranilate dissolved in 20 mL of chloroform was added 3.2 mL (0.039 mol) of pyridine followed by 2.733 g (0.013 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 white solid was washed with ether and dried in vacuo to provide 3.7 g (87%) of the desired sulfonamide. CI Mass Spec: 322 (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 white solid was washed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-416ea893809444bca5e7a77caf10b9e3
Source dataset
uspto-grants-2001_07
Patent number
US06268504B1

Reaction notes

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