p-Toluenesulfonic acid → 2-(1,3-Dioxan-2-yl)thiazole

HRID 989441Notes

Reaction equation

HRID 989441 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][N:7]=1)=[O:2].[CH2:8](O)[CH2:9][CH2:10][OH:11].CC1C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:2]1[CH2:8][CH2:9][CH2:10][O:11][CH:1]1[C:3]1[S:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 225025592-(1,3-Dioxan-2-yl)thiazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-formylthiazole (10 g, 88 mmol), 1,3-propanediol (8 mL) and p-TsOH (100 mg) in benzene (110 mL) was heated at reflux temperature for 15 h with removal of water using a Dean-Stark apparatus. The mixture was cooled to room temperature and washed twice with sat. aq. NaHCO3, twice with water and concentrated. The resulting solid was crystallized from hexane to provide 2-(1,3-Dioxan-2-yl)thiazole as a tan solid (10.4 g).

Workup

  1. temperatureat reflux temperature for 15 h
  2. customwith removal of water using a Dean-Stark apparatus
  3. washwashed twice with sat. aq. NaHCO3, twice with water
  4. concentrationconcentrated
  5. customThe resulting solid was crystallized from hexane

Sources & evidence

ORD record
ord-e0e7d09e0d724fe98cda5945cb409b2c
Source dataset
uspto-grants-2003_10
Patent number
US06639077B2

Reaction notes

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