Chloroacetaldehyde → 4-Hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione
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>[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A 50% aqueous solution of chloroacetaldehyde (28.4 g) is added, at between 20° and 30° C., to a solution of triethylammonium 6-methylpyrid-2-yldithiocarbamate (51.5 g) in distilled water (225 cc). The reaction mixture is stirred for 2 hours at 25° C. The crude product is filtered off, washed five times with distilled water (total 125 cc) and dried in air. The product obtained (37.0 g; m.p. 128° C.) is dissolved in boiling ethanol (250 cc). After filtering the boiling solution and cooling the filtrate for 2 hours at 2° C., the resulting crystals are filtered off, washed three times with ice-cooled ethanol (total 30 cc) and dried under reduced pressure (0.2 mm Hg) at 40° C. 4-Hydroxy-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (29.8 g), melting at 128° C., is thus obtained.
Workup
- filtrationThe crude product is filtered off
- washwashed five times with distilled water (total 125 cc)
- customdried in air
- customThe product obtained (37.0 g; m.p. 128° C.)
- dissolutionis dissolved
- filtrationAfter filtering the boiling solution
- temperaturecooling the filtrate for 2 hours at 2° C.
- filtrationthe resulting crystals are filtered off
- washwashed three times with ice-
- temperaturecooled ethanol (total 30 cc)
- customdried under reduced pressure (0.2 mm Hg) at 40° C
Sources & evidence
- ORD record
- ord-2ca7349cbbb24e2388283ba28366f62d
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04167571
Reaction notes
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