Dimethyl Sulfoxide → HCID 21464366, compound

HRID 1940929Notes

Reaction equation

HRID 1940929 reaction equation
CS(C)=O.Cl[S:6]([C:9]1[N:20]=[C:12]2[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([Cl:17])[N:11]2[N:10]=1)(=[O:8])=[O:7].[F:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:23]=1[NH2:24].N1C=CC=CC=1>C(#N)C.O.ClCCl>[F:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:23]=1[NH:24][S:6]([C:9]1[N:20]=[C:12]2[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([Cl:17])[N:11]2[N:10]=1)(=[O:8])=[O:7]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 796472,6-DifluoroanilineHCID 21464365HCID 21464365, compound

Product 1

HCID 21464366HCID 21464366, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Dimethyl sulfoxide (90 microliters, 94 micrograms, 1.2 mmol) was added with stirring to a solution of 2-chlorosulfonyl-5-chloro-8-methoxy[1,2,4]triazolo[1,5-a]pyridine (1.7 g, 6 mmol), 2,6-difluoroaniline (1.6 g, 12 mmol) and pyridine (0.5 g, 6 mmol) in acetonitrile (20 mL) at ambient temperature. The reaction was complete in about 20 min. Dichloromethane and water were added and the solid that separated was collected by filtration. The organic layer was concentrated by evaporation and the residue obtained was washed with water and combined with the earlier obtained solid. The combined solids were then washed with ether and hexane and dried to obtain 1.4 g of the title compound as an off-white powder melting at 190°-191° C. (d).

Workup

  1. customthe solid that separated
  2. filtrationwas collected by filtration
  3. concentrationThe organic layer was concentrated by evaporation
  4. customthe residue obtained
  5. washwas washed with water
  6. customearlier obtained solid
  7. washThe combined solids were then washed with ether and hexane
  8. customdried

Sources & evidence

ORD record
ord-d6a20e1085c84032b6361399916057f6
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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