Pyridine → ST004384

HRID 1069477Notes

Reaction equation

HRID 1069477 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:11][C:12]([F:21])([F:20])[C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].N1C=CC=CC=1>ClCCl.CN(C1C=CN=CC=1)C>[F:11][C:12]([F:20])([F:21])[C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 69222-(Trifluoromethyl)anilineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 693011ST004384

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (400 g, 2.26 moles) was dissolved in dichloromethane (2 L). To this was added o-trifluoromethylaniline (250 mL, 320 g, 1.99 mol), pyridine (222 mL), and DMAP (7.5 g). The resulting solution was stirred at room temperature for 3 days (72 h), then heated to reflux for 1 hour. The cooled solution was then concentrated on the rotary evaporator, with the bath temperature gradually raised to 70° C. The residue was taken up in ether (3 L) and 1N HCl (1.5 L). The ether layer was separated, washed 2×500 mL with 1N HCl, 1×1 L with brine, 1×1 L with saturated sodium bicarbonate, and once more with 1 L of brine. It was then dried over magnesium sulfate, filtered with suction, and concentrated on the rotary evaporator without heat. The product formed fine crystals as the ether evaporated, and when most of the ether was gone, the crystals were slurried with hexane (2 L), collected with suction and dried. Yield 571 g, 84%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. concentrationThe cooled solution was then concentrated on the rotary evaporator, with the bath temperature
  4. temperaturegradually raised to 70° C
  5. customThe ether layer was separated
  6. washwashed 2×500 mL with 1N HCl, 1×1 L with brine, 1×1 L with saturated sodium bicarbonate
  7. dry with materialIt was then dried over magnesium sulfate
  8. filtrationfiltered with suction
  9. concentrationconcentrated on the rotary evaporator
  10. temperaturewithout heat
  11. customThe product formed fine crystals as the ether
  12. customevaporated
  13. customcollected with suction
  14. customdried

Sources & evidence

ORD record
ord-71d62001d8a84c36b145c6c7b77bc67b
Source dataset
uspto-grants-2001_06
Patent number
US06252070B1

Reaction notes

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