Chloromethyl ethyl ketone → 4-Ethyl-3-(6-ethylpyrid-2-yl)-4-hydroxythiazolidine-2-thione

HRID 261201Notes

Reaction equation

HRID 261201 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[S:12])[S-:11])[CH:6]=[CH:5][CH:4]=1)[CH3:2].C([NH+](CC)CC)C.Cl[CH2:21][C:22](=[O:25])[CH2:23][CH3:24]>C(#N)C>[CH2:23]([C:22]1([OH:25])[CH2:21][S:12][C:10](=[S:11])[N:9]1[C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=1)[CH3:24]

Participants

4

Reactant 2

HCID 69219Chloromethyl ethyl ketoneHCID 20393066Triethylammonium 6-ethylpyrid-2-yldithiocarbamate

Product 1

HCID 203930624-Ethyl-3-(6-ethylpyrid-2-yl)-4-hydroxythiazolidine-2-thioneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 4 is followed but starting with triethylammonium (6-ethylpyrid-2-yl)dithiocarbamate (72.0 g) and 1-chlorobutan-2-one (25.5 g) in anhydrous acetonitrile (400 cc) at a maximum temperature of 25° C. The reaction is continued for 4 hours at 20°-25° C. The product is purified by chromatography over silica (470 g; 0.063-0.200 mm) contained in a column 3.8 cm in diameter, eluting with chloroform (5 liters). The chromatographed product (43.0 g) is recrystallised from ethanol (120 cc) to give 4-ethyl-3-(6-ethylpyrid-2-yl)-4-hydroxythiazolidine-2-thione (37.2 g) melting at 84° C.

Workup

  1. customThe product is purified by chromatography over silica (470 g; 0.063-0.200 mm)
  2. washeluting with chloroform (5 liters)
  3. customThe chromatographed product (43.0 g) is recrystallised from ethanol (120 cc)

Sources & evidence

ORD record
ord-7a56f562d79d439d8ae0302ec1712813
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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