Acetic Acid → HCID 21464431, compound

HRID 1898834Notes

Reaction equation

HRID 1898834 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:24]=[C:16]2[C:17]([O:22][CH3:23])=[CH:18][CH:19]=[C:20](Cl)[N:15]2[N:14]=1)(=[O:12])=[O:11].C[O-].[Na+].CS(C)=O.[C:32](O)(=[O:34])C>ClCCl.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:24]=[C:16]2[C:17]([O:22][CH3:23])=[CH:18][CH:19]=[C:20]([O:34][CH3:32])[N:15]2[N:14]=1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 10942334Sodium MethoxideHCID 21464366HCID 21464366, compound

Product 1

HCID 21464431HCID 21464431, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

N-(2,6-Difluorophenyl)-5-chloro-8-methoxy[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide (1.0 g, 2.7 mmol), sodium methoxide (25 percent in methanol, 2.5 mL, 0.58 g, 11 mmol) and dimethyl sulfoxide (20 mL) were mixed with stirring and slowly heated to 70° C. over a 40-min period. After a short reaction period, the reaction mixture was acidified with acetic acid and diluted With dichloromethane and water. The solid that separated was recovered by filtration. The organic layer was separated, was washed several times with water, and was concentrated by evaporation under reduced pressure. The residue obtained was washed with water and combined with the previously obtained solid. The combined solids were washed with ether and hexane and dried to obtain 0.7 g of the title compound as an off-white powder melting at 319°-320° C.(d).

Workup

  1. customAfter a short reaction period
  2. customThe solid that separated
  3. filtrationwas recovered by filtration
  4. customThe organic layer was separated
  5. washwas washed several times with water
  6. concentrationwas concentrated by evaporation under reduced pressure
  7. customThe residue obtained
  8. washwas washed with water
  9. washThe combined solids were washed with ether and hexane
  10. customdried

Sources & evidence

ORD record
ord-5a65190be1f4415399dd2f5108542650
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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