1-Chloro-4-methylpentan-2-one → 4-Hydroxy-4-isobutyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

HRID 261198Notes

Reaction equation

HRID 261198 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:26])[CH2:22][CH:23]([CH3:25])[CH3:24]>C(#N)C>[OH:26][C:21]1([CH2:22][CH:23]([CH3:25])[CH3:24])[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

Participants

4

Reactant 2

HCID 137209281-Chloro-4-methylpentan-2-oneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

Product 1

HCID 203930724-Hydroxy-4-isobutyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thioneYield 59.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 4 is followed but starting with triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (28.5 g) and 1-chloro-4-methylpentan-2-one (13.4 g) in anhydrous acetonitrile (200 cc) at a temperature between 20 and 25° C. The reaction is continued for 2 hours at 20°-25° C. After recrystallisation of the product from diisopropyl ether (390 cc) and filtration of the boiling solution, there is obtained 4-hydroxy-4-isobutyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (16.8 g) melting at 95° C.

Workup

  1. customAfter recrystallisation of the product
  2. filtrationfrom diisopropyl ether (390 cc) and filtration of the boiling solution

Sources & evidence

ORD record
ord-c5e6fa6238bd46d1acdb559987495305
Source dataset
uspto-grants-1979_08
Patent number
US04164579

Reaction notes

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