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

HRID 261194Notes

Reaction equation

HRID 261194 reaction equation
Cl[CH2:2][CH:3]=[O:4].[CH3:5][C:6]1[N:11]=[C:10]([NH:12][C:13](=[S:15])[S-:14])[CH:9]=[CH:8][CH:7]=1.C([NH+](CC)CC)C.C(O)C>O.C(Cl)(Cl)Cl.C(OCC)C>[OH:4][CH:3]1[CH2:2][S:15][C:13](=[S:14])[N:12]1[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:5])[N:11]=1

Participants

7

Reactant 3

HCID 33ChloroacetaldehydeHCID 702EthanolHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

Product 1

HCID 203930514-Hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thioneYield 70.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
2 °C

Procedure

A 50% (by weight) aqueous solution of chloroacetaldehyde (28.4 g) is added, at a maximum temperature of 30° C., to a solution of triethylammonium (6-methylpyrid-2-yl)-dithiocarbamate (51.5 g) in distilled water (225 cc). The reaction is continued for 2 hours at 20°-30° C. The resulting crystals are separated by filtration, washed five times with distilled water (total 125 cc) and dried in air at 20° C. The product obtained (37.0 g; m.p. 127° C.) is dissolved in a mixture of chloroform (600 cc) and diethyl ether (300 cc); the organic solution is washed three times with distilled water (total 450 cc), dried over sodium sulphate, treated with decolorising charcoal (1 g) and evaporated. The crystals obtained (34.0 g; m.p. 128° C.) are dissolved in boiling ethanol (240 cc). After 2 hours cooling at 2° C., the resulting crystals are separated by filtration, washed twice with ice-cold ethanol (total 30 cc) and dried under reduced pressure (0.1 mm.Hg) at 50° C. 4-Hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (28.8 g), melting at 128° C., is thus obtained.

Workup

  1. customThe resulting crystals are separated by filtration
  2. washwashed five times with distilled water (total 125 cc)
  3. customdried in air at 20° C
  4. customThe product obtained (37.0 g; m.p. 127° C.)
  5. washthe organic solution is washed three times with distilled water (total 450 cc)
  6. dry with materialdried over sodium sulphate
  7. additiontreated with decolorising charcoal (1 g)
  8. customevaporated
  9. customThe crystals obtained (34.0 g; m.p. 128° C.)
  10. dissolutionare dissolved
  11. customthe resulting crystals are separated by filtration
  12. washwashed twice with ice-cold ethanol (total 30 cc)
  13. customdried under reduced pressure (0.1 mm.Hg) at 50° C

Sources & evidence

ORD record
ord-7f0d3d4498e944b090d7da634362c323
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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