Dimethyl Sulfoxide → HCID 18985856, compound

HRID 2396688Notes

Reaction equation

HRID 2396688 reaction equation
Cl[S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:17][CH3:18])=[N:9][C:10]3[S:16][CH:15]=[CH:14][C:11]=32)[N:6]=1)(=[O:4])=[O:3].[Cl:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:21]=1[NH2:22].N1C=CC=CC=1.CS(C)=O>C(#N)C>[Cl:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:21]=1[NH:22][S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:17][CH3:18])=[N:9][C:10]3[S:16][CH:15]=[CH:14][C:11]=32)[N:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 118462,6-DichloroanilineHCID 18985859HCID 18985859, compound

Product 1

HCID 18985856HCID 18985856, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chlorosulfonyl-5-methoxythieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (1.5 g, 4.9 mmol) and 2,6-dichloroaniline (1.59 g, 9.8 mmol) were dissolved in 20 mL of acetonitrile and to this was added under nitrogen at ambient temperature with stirring 0.40 mL (4.9 mmol) of pyridine and 0.05 mL of dimethyl sulfoxide. The mixture was allowed to stir overnight and was then concentrated by evaporation under reduced pressure. The residue was flash chromatographed on silica gel and fractions containing the major product were recovered. Evaporation of the solvents under reduced pressure gave a white powder. This was extracted with 200 mL of hexane and the insoluble white solid was dried to obtain 1.0 g of the title compound melting at 224°-226° C. The proton NMR spectra of this was consistent with the assigned structure.

Workup

  1. additionto this was added under nitrogen at ambient temperature
  2. concentrationwas then concentrated by evaporation under reduced pressure
  3. customchromatographed on silica gel and fractions
  4. additioncontaining the major product
  5. customwere recovered
  6. customEvaporation of the solvents under reduced pressure
  7. customgave a white powder
  8. extractionThis was extracted with 200 mL of hexane
  9. customthe insoluble white solid was dried

Sources & evidence

ORD record
ord-3366ca67f4c74cc1ad9ab23a1eea4e1e
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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