Pyridine → HCID 21956316, compound

HRID 840900Notes

Reaction equation

HRID 840900 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 rt and stirred for 16 h. 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 precipatate was filtered and dried under vacuum at 50° C. to yield 5.78 g, 43.9% of 4-amino-N-(4-aminomethylpyridinyl)-benzenesulfonamide: 1H NMR (DMSO-d6): δ8.42 (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)+. The title compound was prepared in 33% yield from 8-ethoxymethylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one and 4-amino-N-(4-aminomethylpyridinyl)-benzenesulfonamide according to Procedure J: 1H NMR (DMSO-d6): δ11.15 (d, 1H), 10.9 (s, 1H), 9.24 (s, 1H), 8.44 (d, 2H), 8.24 (m, 1H), 8.05 (d, 1H), 7.81 (d, 1H), 7.76 (m, 2H), 7.56 (d, 2H), 7.24 (d, 2H), 7.1 (d, 1H), 4.01 (d, 2H); APCI−MS m/z 464 (MH)+.

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 16 h
  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 precipatate was filtered
  14. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-9892c6e07e5d43ec9b80c4589134fbba
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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