Acrolein → HCID 23458244, compound

HRID 1679876Notes

Reaction equation

HRID 1679876 reaction equation
[CH:1]([CH:3]=[CH2:4])=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[S:15])[S-:14])=[N:10][CH:11]=1.C([NH+](CC)CC)C>C(#N)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:1]([OH:2])[CH2:3][CH2:4][S:15][C:13]2=[S:14])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 7847AcroleinHCID 23458243HCID 23458243, compound

Product 1

HCID 23458244HCID 23458244, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of acrolein (17.6 g) in anhydrous acetonitrile (45 cc) is added, at a maximum temperature of 5° C., to a suspension of triethylammonium 5-chloropyrid-2-yldithiocarbamate (91.5 g) in anhydrous acetonitrile (450 cc). The reaction is allowed to proceed for 90 minutes at a maximum temperature of 5° C. The crystals which appear are filtered off, washed with ice-cooled acetonitrile (50 cc) and then four times with distilled water (total 480 cc) and dried in air. The product obtained (38.8 g; m.p.=136°-137° C.) is purified by recrystallisation from acetonitrile (240 cc). 3-(5-Chloropyrid-2-yl)-4-hydroxyperhydro-1,3-thiazine-2-thione (33.2 g), which melts at 141° C., is obtained.

Workup

  1. filtrationThe crystals which appear are filtered off
  2. washwashed with ice-
  3. temperaturecooled acetonitrile (50 cc)
  4. dry with materialfour times with distilled water (total 480 cc) and dried in air
  5. customThe product obtained (38.8 g; m.p.=136°-137° C.)
  6. customis purified by recrystallisation from acetonitrile (240 cc)

Sources & evidence

ORD record
ord-f188f1477be8474daef00328269cf233
Source dataset
uspto-grants-1981_06
Patent number
US04271156

Reaction notes

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