Dimethyl Sulfoxide → HCID 21464401, compound

HRID 1940892Notes

Reaction equation

HRID 1940892 reaction equation
Cl[S:2]([C:5]1[N:14]=[C:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][N:7]2[N:6]=1)(=[O:4])=[O:3].[Cl:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:17]=1[NH2:18].N1C=CC=CC=1.CS(C)=O>C(#N)C.ClCCl>[Cl:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:17]=1[NH:18][S:2]([C:5]1[N:14]=[C:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][N:7]2[N:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 118462,6-DichloroanilineHCID 21464373175965-05-6

Product 1

HCID 21464401HCID 21464401, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chlorosulfonyl-7-methyl[1,2,4]triazolo[1,5-a]pyridine (1.2 g, 0.0052 mol), 2,6-dichloroaniline (1.7 g, 0.010 mol) and pyridine (0.40 g, 0.0052 mol) were dissolved in anhydrous acetonitrile (20 mL). Dimethyl sulfoxide (60 μL, 0.0008 mol) was added with stirring. The reaction was allowed to stir overnight. The volatiles were removed by evaporation under reduced pressure and the residue obtained was taken up in dichloromethane. The resulting mixture was washed well with dilute aqueous hydrochloric acid and the organic solution phase was recovered and concentrated by evaporation under reduced pressure. The resulting residue was triturated with hexane and the solids that formed were recovered by filtration and dried to obtain 0.7 g (38 percent of theory) of the title compound as a tan powder melting at 232°-234° C.

Workup

  1. stirringto stir overnight
  2. customThe volatiles were removed by evaporation under reduced pressure
  3. customthe residue obtained
  4. washThe resulting mixture was washed well with dilute aqueous hydrochloric acid
  5. customthe organic solution phase was recovered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe resulting residue was triturated with hexane
  8. customthe solids that formed
  9. filtrationwere recovered by filtration
  10. customdried

Sources & evidence

ORD record
ord-84db675960e9480c98ee0dadbf11df0d
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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