Water → HCID 13720638, compound

HRID 1701897Notes

Reaction equation

HRID 1701897 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH2:9]([SH:13])[CH2:10][CH2:11][SH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>ClCCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[S:13][CH2:9][CH2:10][CH2:11][S:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80131,3-PropanedithiolHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 13720638HCID 13720638, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of pyridine-2-carboxaldehyde (26.7 g), propane-1,3-dithiol (94.4 g) and paratoluenesulphonic acid (3.7 g) in 1,2-dichloroethane (2500 cc) is kept at the boil for 20 hours so that the water formed is removed by azeotropic distillation. After cooling to 5° C., the reaction mixture is washed twice with an approximately 7 N aqueous solution of potassium hydroxide (540 cc in total) and then four times with distilled water (1400 cc in total). The organic solution is dried over anhydrous sodium sulphate and filtered and the filtrate is concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. 2-(Pyrid-2-yl)-1,3-dithiane (41.9 g) is thus obtained.

Workup

  1. customformed
  2. customis removed by azeotropic distillation
  3. washthe reaction mixture is washed twice with an approximately 7 N aqueous solution of potassium hydroxide (540 cc in total)
  4. dry with materialThe organic solution is dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-09eb264b2d534f8a801cb91ea670bce3
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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