Pyridine → HCID 21956316, compound

HRID 2297858Notes

Reaction equation

HRID 2297858 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C([NH:12][C:13]1[CH:22]=[CH:21][C:16]([S:17](Cl)(=[O:19])=[O:18])=[CH:15][CH:14]=1)(=O)C.[N:23]1C=CC=CC=1>>[NH2:12][C:13]1[CH:22]=[CH:21][C:16]([S:17]([NH:23][C:5]2[CH:4]=[C:3]([CH2:2][NH2:1])[CH:8]=[CH:7][N:6]=2)(=[O:19])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8481N-Acetylsulfanilyl chlorideHCID 773174-Pyridinemethanamine

Product 1

HCID 21956316HCID 21956316, compoundYield 43.9%

Conditions

Temperature
0 °C

Procedure

To a 250 ml round bottom flask was added 50 ml of dry pyridine, 4-(aminomethyl) pyridine (10.4 g, 50.0 mmol) and a magnetic stir bar. The mixture was stirred and cooled to 0° C. under nitrogen followed by the addition of N-acetylsulfanilyl chloride (12.8 g, 55.0 mmol). The resultant mixture was stirred at 0° C. under nitrogen for 5 min, and the reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was concentrated to a thick residue and poured onto about 500 g of ice and water. The residue in the flask was rinsed into the ice and water with 25 ml of MeOH to precipitate the N-acetyl sulfanilamide. The resultant precipitate was filtered, washed with excess water and dried under vacuum at 50° C. The solid was suspended in 75 ml of 1N hydrochloric acid and heated to 100° C. until all starting material had been consumed. The reaction mixture was cooled and neutralized with ammonium hydroxide. The precipitate was filtered and dried under vacuum at 50° C. to yield 5.78 g, 43.9% of the compound: 1H NMR (DMSO-d6): δ 8.42 (d, 2H), 7.76 (t, 1H), 7.39 (d, 2H), 7.22 (d, 2H), 6.56 (d, 2H), 5.91 (s, 2H), 3.89 (d, 2H); APCI-MS m/z 264 (MH)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. concentrationThe reaction mixture was concentrated to a thick residue
  4. additionpoured onto about 500 g of ice and water
  5. washThe residue in the flask was rinsed into the ice and water with 25 ml of MeOH
  6. customto precipitate the N-acetyl sulfanilamide
  7. filtrationThe resultant precipitate was filtered
  8. washwashed with excess water
  9. customdried under vacuum at 50° C
  10. temperatureheated to 100° C. until all starting material
  11. customhad been consumed
  12. temperatureThe reaction mixture was cooled
  13. filtrationThe precipitate was filtered
  14. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-2f43ec77ddfa47e5b3d021d8498fceb2
Source dataset
uspto-grants-2002_12
Patent number
US06492398B1

Reaction notes

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