Acetic Acid → HCID 21464346, compound

HRID 1898804Notes

Reaction equation

HRID 1898804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:23]=[C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[C:20](Cl)[N:15]2[N:14]=1)(=[O:12])=[O:11].C[O-].[Na+].[C:27](O)(=[O:29])C.CCOCC>CO.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:23]=[C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[C:20]([O:29][CH3:27])[N:15]2[N:14]=1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 21464419HCID 21464419, compound

Product 1

HCID 21464346HCID 21464346, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(2,6-Dichlorophenyl)-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide (3.0 g, 0.0077 mol) and 25 percent sodium methoxide in methanol (12 mL, 2.8 g, 0.050 mol) were combined in methanol (100 mL) and heated to reflux with stirring for 2 hours. The reaction mixture was cooled and acidified with acetic acid and the volatiles were removed by evaporation under reduced pressure. The residue obtained was diluted with dichloromethane and the mixture was washed with water. The organic solution phase was filtered and the filtrate was concentrated by evaporation under reduced pressure. The residue obtained was mixed with ether and filtered to recover the solids. The solids were dried to obtain 2.6 g (87 percent of theory) of the title compound as a white powder melting at 269°-270° C.(d).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. customthe volatiles were removed by evaporation under reduced pressure
  5. customThe residue obtained
  6. washthe mixture was washed with water
  7. filtrationThe organic solution phase was filtered
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. customThe residue obtained
  10. filtrationfiltered
  11. customto recover the solids
  12. customThe solids were dried

Sources & evidence

ORD record
ord-19214abbf9a14ef7a60a2eb0f1c538de
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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