Pyridine → HCID 673877, compound

HRID 1162460Notes

Reaction equation

HRID 1162460 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 673877HCID 673877, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL round-bottomed flask was added 2-amino-5-bromopyridine (15.0 g, 86.7 mmol, Aldrich, St. Louis, Mo.), pyridine (150 mL, 1858 mmol) and finally para-toluenesulfonyl chloride (24.8 g, 130 mmol, Aldrich, St. Louis, Mo.) at rt. The mixture was stirred at 90° C. After 24 h, the mixture was allowed to cool to rt and then poured into water (600 mL). A precipitate formed and the mixture was stirred for 15 min and then filtered. The filtercake was washed with water and hexane and then dried under vacuum to afford the title compound as an off-white solid (27.8 g, 98%) that was carried on without further purification.

Workup

  1. temperatureto cool to rt
  2. customA precipitate formed
  3. stirringthe mixture was stirred for 15 min
  4. filtrationfiltered
  5. washThe filtercake was washed with water and hexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9f61bec200b041b68a809b39c79a01eb
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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