Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-1,3-thiazole

HRID 458422Notes

Reaction equation

HRID 458422 reaction equation
C1C=CC=CC=1.[S:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=[O:13].[CH2:14](O)[CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.O>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[C:8]1[S:7][CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 152051582-(1,3-Dioxolan-2-yl)-1,3-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A benzene (10 mL) solution of 2-thiazole carboxaldehyde (5.00 g 44.19 mmol), ethylene glycol (7.40 mL, 132.58 mmol) and p-toluenesulfonic acid monohydrate (1.50 g, 7.89 mmol) was refluxed with azeotropic removal of H2O for 3 h and then cooled to ambient temperature. The reaction mixture was diluted with Et2O and the organics washed with sat'd NaHCO3, brine and then dried (MgSO4), filtered and concentrated to provide the title compound as a reddish oil. 1H NMR (CDCl3, 400 MHz) δ 7.79 (d, J=3.1 Hz, 1H), 7.35 (d, J=3.1 Hz, 1H), 6.13 (s, 1H), 4.16–4.01 (m, 4H).

Workup

  1. washthe organics washed with sat'd NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f8456771cad741c4b0836a4debac2eae
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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