Ethylene Glycol → HCID 15665807, compound

HRID 2111929Notes

Reaction equation

HRID 2111929 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Cl:7])[N:6]=1.[CH2:10](O)[CH2:11][OH:12].C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:3][C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[C:5]([Cl:7])[N:6]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehyde

Product 1

HCID 15665807HCID 15665807, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Add p-toluenesulfonic acid monohydrate (1.70 g, 8.94 mmol) to a stirred solution of 2,4-dichloro-thiazole-5-carbaldehyde (21.05 g, 116 mmol), ethylene glycol (20.0 mL, 359 mmol), and anhydrous toluene (300 mL). Add a Dean-Stark trap and heat the reaction to reflux under nitrogen for 7 h. Cool the reaction and pour it into 10% sodium carbonate (300 mL). Extract with ethyl acetate (3×150 mL) and wash with brine (150 mL). Dry the ethyl acetate over sodium sulfate and then filter off the sodium sulfate. Concentrate on a rotary evaporator and purify the crude product by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes to yield 24.77 g (95%) of 2,4-dichloro-5-[1,3]dioxolan-2-yl-thiazole: mass spectrum (ion spray): m/z=225.9 (M+1); 1H NMR (CDCl3): δ=6.08 (s, 1H), 4.19-4.03 (m, 4H).

Workup

  1. additionAdd a Dean-Stark trap
  2. temperatureheat
  3. customthe reaction
  4. temperatureto reflux under nitrogen for 7 h
  5. temperatureCool
  6. customthe reaction
  7. extractionExtract with ethyl acetate (3×150 mL)
  8. washwash with brine (150 mL)
  9. dry with materialDry the ethyl acetate over sodium sulfate
  10. filtrationfilter off the sodium sulfate
  11. concentrationConcentrate on a rotary evaporator
  12. custompurify the crude product by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e1a585d1426642f1ad49a0325a401396
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

Loading…