Acetic Acid → HCID 21464438, compound

HRID 1940903Notes

Reaction equation

HRID 1940903 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:29]=[C:21]2[CH:22]=[C:23](Cl)[CH:24]=[C:25]([O:26][CH3:27])[N:20]2[N:19]=1)(=[O:17])=[O:16].[C:30](O)(=[O:32])C>CS(C)=O.ClCCl>[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:29]=[C:21]2[CH:22]=[C:23]([O:32][CH3:30])[CH:24]=[C:25]([O:26][CH3:27])[N:20]2[N:19]=1)(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 21464355HCID 21464355, compound

Product 1

HCID 21464438HCID 21464438, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium methoxide in methanol (3.0 mL of 25 percent solution, 0.71 g, 0.013 mol) was added to a solution of N-(2,6-dichlorophenyl)-5-methoxy-7-chloro[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide (0.66 g, 0.0016 mol) in dimethyl sulfoxide (30 mL) with stirring over several hours. The mixture was allowed to react and 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 chromatographed on silica gel starting with 0.5 percent acetic acid in dichloromethane and gradually increasing the strength to 0.5 percent acetic acid plus 1.0 percent ethanol in dichloromethane. The product fractions were concentrated by evaporation under reduced pressure to obtain 118 mg (13 percent of theory) of the title compound as a pale yellow powder melting at 252°-253° C.(d).

Workup

  1. customto react
  2. customThe resulting organic phase was recovered
  3. washwashed with water
  4. customthe volatiles were removed by evaporation under reduced pressure
  5. customThe residue obtained
  6. customwas chromatographed on silica gel starting with 0.5 percent acetic acid in dichloromethane
  7. temperaturegradually increasing the strength to 0.5 percent acetic acid plus 1.0 percent ethanol in dichloromethane
  8. concentrationThe product fractions were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4ce31ffa726343adaad6e233295b420e
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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