Ethanol → 4-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

HRID 261195Notes

Reaction equation

HRID 261195 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][C:7]1[N:12]=[C:11]([NH:13][C:14](=[S:16])[S-:15])[CH:10]=[CH:9][CH:8]=1.C([NH+](CC)CC)C.C(O)C>CN(C)C=O>[OH:5][C:3]1([CH3:4])[CH2:2][S:16][C:14](=[S:15])[N:13]1[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:6])[N:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6571ChloroacetoneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

Product 1

HCID 203930694-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2 °C

Procedure

Chloroacetone (13.9 cc) is added to a solution of triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (50.0 g) in dimethylformamide (250 cc) at a temperature between 15 and 23° C. The reaction is continued for 3 hours at 20°-23° C. After filtration and evaporation of the dimethylformamide under reduced pressure (0.1 mm.Hg) at 45° C., the residual oil is dissolved in ethyl acetate (500 cc); the organic solution is washed with distilled water (100 cc), dried over sodium sulphate, treated with decolorising charcoal (2 g) and evaporated. The crystals obtained (38.0 g; m.p. 150°-153° C.) are dissolved in boiling ethanol (520 cc). After 2 hours cooling at 2° C., the resulting crystals are separated by filtration, washed twice with ice-cold ethanol (total 80 cc) and dried under reduced pressure (0.1 mm.Hg) at 45° C. 4-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (24.9 g), melting at 156° C., is obtained.

Workup

  1. filtrationAfter filtration and evaporation of the dimethylformamide under reduced pressure (0.1 mm.Hg) at 45° C.
  2. dissolutionthe residual oil is dissolved in ethyl acetate (500 cc)
  3. washthe organic solution is washed with distilled water (100 cc)
  4. dry with materialdried over sodium sulphate
  5. additiontreated with decolorising charcoal (2 g)
  6. customevaporated
  7. customThe crystals obtained (38.0 g; m.p. 150°-153° C.)
  8. dissolutionare dissolved
  9. customthe resulting crystals are separated by filtration
  10. washwashed twice with ice-cold ethanol (total 80 cc)
  11. customdried under reduced pressure (0.1 mm.Hg) at 45° C

Sources & evidence

ORD record
ord-1b6f302e718a42a8827d125a22a0379b
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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