Methanesulfonic Acid → HCID 13365927, compound

HRID 1154352Notes

Reaction equation

HRID 1154352 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[CH2:2][C:3](=O)[CH2:4][CH2:5][CH3:6].[CH2:13]([SH:16])[CH2:14][SH:15].CS(O)(=O)=O>C(Cl)Cl>[CH2:4]([C:3]1([CH2:2][CH2:1][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[S:16][CH2:13][CH2:14][S:15]1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 109021,2-EthanedithiolHCID 13365926HCID 13365926, compound

Product 1

HCID 13365927HCID 13365927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution 1-(hexan-3-on-1-yl)imidazole (1.00 g) was stirred with ethane-1,2-dithiol (1 ml) at room temperature and then 1 ml of methanesulfonic acid was added in portions with cooling. After 15 minutes, 20 ml of methylene chloride was added and the mixture stirred for 4 hours. The reaction mixture was poured into 300 ml of methylene chloride which solution was washed with 3×100 ml 5% sodium hydroxide, 1×100 ml water and the organic layer dried over magnesium sulfate. Removal of the solvent afforded an oil which was chromatographed on silica gel, eluting with hexane, 50% hexane/ethyl acetate and ethyl acetate to yield 1.2 g of 1-[2-(2-propyl-1,3-dithiolan-2-yl)ethyl]imidazole. 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-(propyl-1,3-dithiolan-2-yl)ethyl]imidazole hydrochloride, m.p. 118° -121° C.

Workup

  1. temperaturewith cooling
  2. washwas washed with 3×100 ml 5% sodium hydroxide, 1×100 ml water
  3. dry with materialthe organic layer dried over magnesium sulfate
  4. customRemoval of the solvent
  5. customafforded an oil which
  6. customwas chromatographed on silica gel
  7. washeluting with hexane, 50% hexane/ethyl acetate and ethyl acetate

Sources & evidence

ORD record
ord-ed2fb85aef4649e6b2b3909fe4e461d7
Source dataset
uspto-grants-1984_12
Patent number
US04489087

Reaction notes

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