Cyclohexane → 4-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thione

HRID 261197Notes

Reaction equation

HRID 261197 reaction equation
Cl[CH2:2][C:3](=[O:7])[CH2:4][CH2:5][CH3:6].[CH3:8][C:9]1[N:14]=[C:13]([NH:15][C:16](=[S:18])[S-:17])[CH:12]=[CH:11][CH:10]=1.C([NH+](CC)CC)C.C1CCCCC1>C(#N)C>[OH:7][C:3]1([CH2:4][CH2:5][CH3:6])[CH2:2][S:18][C:16](=[S:17])[N:15]1[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:8])[N:14]=1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 112864631-Chloropentan-2-oneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

Product 1

HCID 203930574-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thioneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

1-Chloropentan-2-one (12.1 g) is added to a suspension of triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (28.5 g) in anhydrous acetonitrile (200 cc) at a temperature between 15° and 25° C. The reaction is continued for 2 hours at 20°-25° C. The insoluble triethylamine hydrochloride is removed by filtration and washed twice with diethyl ether (60 cc. total). The solvents are evaporated under reduced pressure (20 mm.Hg) at 40° C. The residual oil is dissolved in a mixture of diethyl ether (100 cc) and methylene chloride (50 cc); the organic solution is washed twice with distilled water (total 100 cc), dried over sodium sulphate and evaporated. The crystals obtained (25.4 g; m.p. about 70° C.) are dissolved in boiling cyclohexane (500 cc) and the boiling solution is filtered. After cooling for 1 hour at about 10° C., the resulting crystals are separated by filtration, washed twice with cyclohexane (total 120 cc) cooled to 10° C., and dried under reduced pressure (0.1 mm.Hg) at 40° C. 4-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thione (21.6 g), melting at 83° C., is thus obtained.

Workup

  1. customThe insoluble triethylamine hydrochloride is removed by filtration
  2. washwashed twice with diethyl ether (60 cc. total)
  3. customThe solvents are evaporated under reduced pressure (20 mm.Hg) at 40° C
  4. dissolutionThe residual oil is dissolved in a mixture of diethyl ether (100 cc) and methylene chloride (50 cc)
  5. washthe organic solution is washed twice with distilled water (total 100 cc)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe crystals obtained (25.4 g; m.p. about 70° C.)
  9. dissolutionare dissolved
  10. filtrationthe boiling solution is filtered
  11. customthe resulting crystals are separated by filtration
  12. washwashed twice with cyclohexane (total 120 cc)
  13. temperaturecooled to 10° C.
  14. customdried under reduced pressure (0.1 mm.Hg) at 40° C

Sources & evidence

ORD record
ord-0b779f0c9f4240cd84a0040ec3124e21
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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