Methanesulfonic Acid → HCID 13363494, compound

HRID 1248428Notes

Reaction equation

HRID 1248428 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH:10]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH3:11].CS(O)(=O)=O.[CH2:23]([SH:26])[CH2:24][SH:25].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:10]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH3:11])[S:26][CH2:23][CH2:24][S:25]1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 109021,2-EthanedithiolHCID 11430Potassium CarbonateHCID 3023813HCID 3023813, compound

Product 1

HCID 13363494HCID 13363494, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 6 parts of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-propanone and 30 parts of methanesulfonic acid was stirred till all solid entered solution. After cooling, 5.5 parts of 1,2-ethanedithiol were added while nitrogen gas was introduced. The whole was stirred overnight at room temperature. The reaction mixture was diluted with trichloromethane till a volume of 150 parts. This solution was added dropwise to a vigorously stirred solution of potassium carbonate in water. The organic phase was separated, washed with water, dried, filtered and evaporated. The oily residue was converted into the nitrate salt in 2-propanol. 2,2'-Oxybispropane was added till turbid and the formed salt was allowed to crystallize. It was filtered off and dried, yielding 6 parts of 2-(2,4-dichlorophenyl)-2-[1-(1H-imidazol-1-yl)ethyl]-1,3-dithiolane; mp. 141.9° C. (compound 29).

Workup

  1. temperatureAfter cooling
  2. additionwas introduced
  3. stirringThe whole was stirred overnight at room temperature
  4. customThe organic phase was separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. addition2,2'-Oxybispropane was added till turbid
  10. customto crystallize
  11. filtrationIt was filtered off
  12. customdried

Sources & evidence

ORD record
ord-6690da7c21354d16a7357b13ee1210d0
Source dataset
uspto-grants-1985_06
Patent number
US04524110

Reaction notes

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