Chloromethyl ethyl ketone → 4-Ethyl-4-hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

HRID 261196Notes

Reaction equation

HRID 261196 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[S:11])[S-:10])[CH:5]=[CH:4][CH:3]=1.C([NH+](CC)CC)C.Cl[CH2:20][C:21](=[O:24])[CH2:22][CH3:23]>O>[CH2:22]([C:21]1([OH:24])[CH2:20][S:11][C:9](=[S:10])[N:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[CH3:23]

Participants

4

Reactant 2

HCID 69219Chloromethyl ethyl ketoneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

Product 1

HCID 203930734-Ethyl-4-hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thioneYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure of Example 1 is followed but starting with triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (71.0 g) and 1-chlorobutan-2-one (26.6 g) in distilled water (300 cc) at 20° C. The reaction is carried out for 3 hours at 20° C. After recrystallisation of the product from ethanol (250 cc), there is obtained 4-ethyl-4-hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (45.0 g) melting at 118° C.

Workup

  1. customAfter recrystallisation of the product from ethanol (250 cc)

Sources & evidence

ORD record
ord-57b0ed6328d549958ab32c2b16a5e60c
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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