Sodium Carbonate → HCID 11610203, compound

HRID 2198784Notes

Reaction equation

HRID 2198784 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[CH2:18]([SH:21])[CH2:19][SH:20].C(=O)([O-])[O-].[Na+].[Na+]>CS(O)(=O)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:11][N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[S:21][CH2:18][CH2:19][S:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 109021,2-EthanedithiolHCID 110103354-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-one

Product 1

HCID 11610203HCID 11610203, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole (2.49 g) in 98% methanesulfonic acid (10 ml) was treated with ethane-1,2-dithiol (6 ml) and the mixture stirred overnight at room temperature. The resulting mixture was poured into excess aqueous sodium carbonate, extracted with ether (3×20 ml), the extracts washed, dried (MgSO4) and the ether evaporated. The residue was taken up in a small volume of ether and treated with ethereal hydrogen chloride until precipitation was complete. The resulting precipitate was filtered off and recrystallized from methanol/ethyl acetate, to give 1-[[2-(2-(4-chlorophenyl)ethyl)-1,3-dithiolan-2-yl]methyl]imidazole hydrochloride, m.p. 206.5°-208° C. Similarly proceeding as above, but substituting the appropriate ethan-1,2-dithiol and the appropriate ketone as exemplified in Preparations 1, 2, 3 or 4 in place of 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole there may be prepared, for example, the following compounds:

Workup

  1. extractionextracted with ether (3×20 ml)
  2. washthe extracts washed
  3. dry with materialdried (MgSO4)
  4. customthe ether evaporated
  5. additiontreated with ethereal hydrogen chloride until precipitation
  6. filtrationThe resulting precipitate was filtered off
  7. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-5da86096e18c4925afdbbf2613ed84f8
Source dataset
uspto-grants-1982_11
Patent number
US04359475

Reaction notes

Loading…