Chloroacetaldehyde → HCID 23458681, compound

HRID 1679937Notes

Reaction equation

HRID 1679937 reaction equation
Cl[CH2:2][CH:3]=[O:4].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[S:14])[S-:13].C([NH+](CC)CC)C>CN(C)C=O>[OH:4][CH:3]1[CH2:2][S:14][C:12](=[S:13])[N:11]1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 15899924HCID 15899924, compound

Product 1

HCID 23458681HCID 23458681, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2 °C

Procedure

A 50% by weight aqueous solution of chloroacetaldehyde (37.7 g) is added at 10° C., to a solution of triethylammonium pyrid-2-yldithiocarbamate (65.4 g) in dimethylformamide (300 cc). The reaction is allowed to proceed for 16 hours at 20° C. After evaporating off the solvents under pressure (0.1 mm Hg) at 50° C., the residual oil is treated with chloroform (750 cc). The chloroform solution is washed twice with distilled water (200 cc in total), dried over sodium sulphate and evaporated. The oily residue (38 g) is dissolved in boiling ethanol (180 cc), and boiling isopropyl ether (180 cc) and decolourising charcoal (1 g) are added. After filtering the boiling solution and then cooling for 2 hours at 2° C., the crystals which have appeared are filtered off, washed with an ice-cooled mixture (50 cc in total) of ethanol (25 cc) and isopropyl ether (25 cc) and dried under reduced pressure (0.1 mm Hg) at 45° C. 4-Hydroxy-3-(pyrid-2-yl)thiazolidine-2-thione (17.8 g), which melts at 110° C., is thus obtained.

Workup

  1. customAfter evaporating off the solvents under pressure (0.1 mm Hg) at 50° C.
  2. additionthe residual oil is treated with chloroform (750 cc)
  3. washThe chloroform solution is washed twice with distilled water (200 cc in total)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. dissolutionThe oily residue (38 g) is dissolved
  7. additionare added
  8. filtrationAfter filtering the boiling solution
  9. filtrationthe crystals which have appeared are filtered off
  10. washwashed with an ice-
  11. temperaturecooled mixture (50 cc in total) of ethanol (25 cc) and isopropyl ether (25 cc)
  12. customdried under reduced pressure (0.1 mm Hg) at 45° C

Sources & evidence

ORD record
ord-b554b11e8ca54195a145d745d5bdc41c
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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