Pyridine → HCID 57551242, compound

HRID 1644658Notes

Reaction equation

HRID 1644658 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1.[NH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1.N1C=CC=CC=1>>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 5745904-Bromo-2,5-difluorobenzenesulfonyl Chloride

Product 1

HCID 57551242HCID 57551242, compoundYield 21.7%

Procedure

4-BROMO-2,5-DIFLUOROBENZENESULFONYL CHLORIDE (10.0 g, 0.0345 mol) and 2-AMINOTHIAZOLE (3.80 g, 0.0379 mol) were mixed in Pyridine (40 mL, 0.5 mol). The reaction was allowed to stir at room temperature for 9 days. The reaction was concentrated in vacuo to a total volume of approximately 40 mL. The residue was triturated with 1N HCl (aq). Acetonitrile was added until the precipitate became free-flowing. The solid was collected by filtration and rinsed with acetonitrile then ethyl ether. The solid was dissolved in boiling acetonitrile and treated with activated carbon then filtered through a celite pad. The filtrate was reduced to ⅓ its original volume by distillation. The mixture was cooled to room temperature. The crystals were collected by filtration and rinsed with ethyl ether. Vacuum drying gave 2.66 g of off-white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo to a total volume of approximately 40 mL
  2. customThe residue was triturated with 1N HCl (aq)
  3. additionAcetonitrile was added until the precipitate
  4. filtrationThe solid was collected by filtration
  5. washrinsed with acetonitrile
  6. dissolutionThe solid was dissolved
  7. additiontreated with activated carbon
  8. filtrationthen filtered through a celite pad
  9. distillationby distillation
  10. temperatureThe mixture was cooled to room temperature
  11. filtrationThe crystals were collected by filtration
  12. washrinsed with ethyl ether
  13. customVacuum drying

Sources & evidence

ORD record
ord-f22fbf17ea85438fb1f96842044fd864
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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