Dimethyl Sulfoxide → HCID 15003657, compound

HRID 373455Notes

Reaction equation

HRID 373455 reaction equation
[I-].[Na+].C[Si](Cl)(C)C.[Cl:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:10]=1[NH2:11].C(N(CC)CC)C.[Cl:24][C:25]1[C:26]2[N:27]([N:34]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[N:36]=2)[C:28]([CH3:33])=[N:29][C:30]=1[O:31][CH3:32].CS(C)=O>C(#N)C>[Cl:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:10]=1[NH:11][S:37]([C:35]1[N:36]=[C:26]2[N:27]([C:28]([CH3:33])=[N:29][C:30]([O:31][CH3:32])=[C:25]2[Cl:24])[N:34]=1)(=[O:38])=[O:39]

Participants

8

Reactant 6

HCID 679Dimethyl SulfoxideHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 118462,6-DichloroanilineHCID 15003646HCID 15003646, compound

Product 1

HCID 15003657HCID 15003657, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Anhydrous sodium iodide (11.7 g, 0.078 mol) was placed in 50 ml of dry acetonitrile and 8.5 g (0.078 mol) of trimethylsilyl chloride added with stirring. To this was added 6.3 g (0.039 mol) of 2,6-dichloroaniline and 7.9 g (0.078 mol) of triethylamine. The mixture was stirred at ambient temperature for 30 min and then the volatiles were carefully removed by evaporation under reduced pressure and the residue diluted with ether and filtered. The contents of this solution appeared to be N-trimethylsilyl-2,6-dichloroaniline of about 97 percent purity by GLC analysis. The ether precipitation of insolubles was repeated and the ether was removed by evaporation under reduced pressure. The residue was mixed with 50 ml of dry acetonitrile, 3.9 g (0.013 mol) of 8-chloro-2-chlorosulfonyl-7-methoxy-5-methyl-1,2,4-triazolo[1,5-c]pyrimidine, and 0.2 ml (0.003 mol) of dimethylsulfoxide and the mixture stirred overnight. The resulting mixture was concentrated under reduced pressure and the solid residue was mixed with hexane and water and filtered. The residue was then dissolved in 400 ml of methylene chloride and resulting solution was twice extracted with water, dried over sodium sulfate and filtered. It was then concentrated under reduced pressure and the residue was mixed with hexane, collected by filtration, and dried to obtain 3.3 g (60 percent of theory) of the title compound as a pale yellow powder melting at 255°-256° C. with decomposition.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 min
  2. customthe volatiles were carefully removed by evaporation under reduced pressure
  3. additionthe residue diluted with ether
  4. filtrationfiltered
  5. customThe ether precipitation of insolubles
  6. customthe ether was removed by evaporation under reduced pressure
  7. stirringthe mixture stirred overnight
  8. concentrationThe resulting mixture was concentrated under reduced pressure
  9. additionthe solid residue was mixed with hexane and water
  10. filtrationfiltered
  11. dissolutionThe residue was then dissolved in 400 ml of methylene chloride
  12. customresulting solution
  13. extractionwas twice extracted with water
  14. dry with materialdried over sodium sulfate
  15. filtrationfiltered
  16. concentrationIt was then concentrated under reduced pressure
  17. additionthe residue was mixed with hexane
  18. filtrationcollected by filtration
  19. customdried

Sources & evidence

ORD record
ord-b1acd545cecf40aca554b752cf620bac
Source dataset
uspto-grants-1992_11
Patent number
US05163995

Reaction notes

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