1,3-Propanediol → 2-(1,3-Dioxan-2-yl)thiazole

HRID 1251133Notes

Reaction equation

HRID 1251133 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[CH2:8](O)[CH2:9][CH2:10][OH:11]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:7]1[CH2:8][CH2:9][CH2:10][O:11][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 104421,3-PropanediolHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 225025592-(1,3-Dioxan-2-yl)thiazoleYield 73%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2-Thiazolecarboxaldehyde (1 g) was dissolved in toluene (50 ml), followed by the addition of trimethylene glycol (3.36 g) and p-toluenesulfonic acid (17 mg). The resulting mixture was heated under reflux with a Dean-Stark apparatus for 4 hr. After cooling as it was, the reaction mixture was washed sequentially with an aqueous solution of saturated sodium bicarbonate and brine, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a brown solid (1.104 g, yield; 73%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux with a Dean-Stark apparatus for 4 hr
  3. temperatureAfter cooling as it
  4. washthe reaction mixture was washed sequentially with an aqueous solution of saturated sodium bicarbonate and brine
  5. dry with materialdried (over MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-c05fd718d93b4acbb76712d26b7c5708
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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