Pyridine → HCID 21956316, compound

HRID 1935557Notes

Reaction equation

HRID 1935557 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 9, 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 1 N 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): 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)+. 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): δ 11.15 (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. stirringwas stirred at 0° C. under nitrogen for 5 min
  2. temperatureto warm to rt
  3. stirringstirred for 16 h
  4. concentrationThe reaction mixture was concentrated to a thick residue
  5. additionpoured onto about 500 g of ice and water
  6. washThe residue in the flask was rinsed into the ice and water with 25 ml of MeOH
  7. customto precipitate the N-acetyl sulfanilamide
  8. filtrationThe resultant precipitate was filtered
  9. washwashed with excess water
  10. customdried under vacuum at 50° C
  11. temperatureheated to 100° C. until all starting material
  12. customhad been consumed
  13. temperatureThe reaction mixture was cooled
  14. filtrationThe precipatate was filtered
  15. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-a87180de1aa34a1a881e5eec9259a48d
Source dataset
uspto-grants-2002_05
Patent number
US06387919B1

Reaction notes

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