Methanol → HCID 19975240, compound

HRID 1450149Notes

Reaction equation

HRID 1450149 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[C:17](Cl)=[N:18][CH:19]=[C:20](Br)[N:15]2[N:14]=1)(=[O:12])=[O:11].[CH3:24][O-:25].[Na+].[CH3:27][OH:28]>C(#N)C>[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[C:17]([O:28][CH3:27])=[N:18][CH:19]=[C:20]([O:25][CH3:24])[N:15]2[N:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 19975239HCID 19975239, compound

Product 1

HCID 19975240HCID 19975240, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 0.42 g (0.92 mmol) of N-(2,6-dichlorophenyl)-5-bromo-8-chloro[1,2,4]triazolo[1,5-a]-pyrazine-2-sulfonamide in 30 mL of dry acetonitrile was combined with 2.8 mL (5.6 mmol) of a 2M solution of sodium methoxide in methanol and the mixture was warmed to 40° C. under a nitrogen atmosphere with stirring. After 24 hours, the reaction was quenched with 1 mL of glacial acetic acid and the solvent was removed under reduced pressure. The residue was extracted portionwise with up to 100mL of tetrahydrofuran and the cloudy extract obtained was filtered and concentrated by evaporation under reduced pressure. The title compound was isolated from the residue obtained by flash column chromatography on silica gel using a 2 to 10 percent ethanol/dichloromethane gradient as eluent. The title compound, which was the least polar of the three compounds present, was further purified by extraction with warm methanol and diethyl ether mixtures to obtain 46 mg (12 percent of theory) as a white powder melting above 250° C. with decomposition.

Workup

  1. customthe reaction was quenched with 1 mL of glacial acetic acid
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residue was extracted portionwise with up to 100mL of tetrahydrofuran
  4. extractionthe cloudy extract
  5. customobtained
  6. filtrationwas filtered
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8bf524052c9a416c9dd7af14018fc1ae
Source dataset
uspto-grants-1997_02
Patent number
US05602075

Reaction notes

Loading…