Acetic Acid → HCID 21464355, compound

HRID 1940902Notes

Reaction equation

HRID 1940902 reaction equation
C[O-].[Na+].CO.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[NH:14][S:15]([C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([Cl:27])[CH:24]=[C:25](Cl)[N:20]2[N:19]=1)(=[O:17])=[O:16].[C:29](O)(=[O:31])C>CS(C)=O.ClCCl.CCCCCC>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[NH:14][S:15]([C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([Cl:27])[CH:24]=[C:25]([O:31][CH3:29])[N:20]2[N:19]=1)(=[O:17])=[O:16]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 21464351HCID 21464351, compound

Product 1

HCID 21464355HCID 21464355, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Sodium methoxide in methanol (1.1 mL of 25 percent solution, 0.26 g, 0.005 mol) was added to a solution of N-(2,6-dichlorophenyl)-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide (0.9 g, 0.02 mol) in dimethyl sulfoxide (30 mL) at ambient temperature with stirring. The reaction was complete in a few minutes, but was stirred for 30 min. The mixture was then acidified with acetic acid and diluted with dichloromethane. The resulting organic phase was recovered and washed with water and the volatiles were removed by evaporation under reduced pressure. The residue obtained was mixed with hexane and the insoluble solids were collected by filtration and dried to obtain 0.8 g (90 percent of theory) of the title compound as a light tan powder melting at 232°-234° C.(d).

Workup

  1. waitThe reaction was complete in a few minutes
  2. stirringwas stirred for 30 min
  3. customThe resulting organic phase was recovered
  4. washwashed with water
  5. customthe volatiles were removed by evaporation under reduced pressure
  6. customThe residue obtained
  7. filtrationthe insoluble solids were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f6e16fb264ca4bb29ffc1703c42cb6f9
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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