Ethylene Glycol → HCID 15665807, compound

HRID 2111912Notes

Reaction equation

HRID 2111912 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[Cl:5][C:6]1[S:7][C:8]([CH:12]=O)=[C:9]([Cl:11])[N:10]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:5][C:6]1[S:7][C:8]([CH:12]2[O:4][CH2:1][CH2:2][O:3]2)=[C:9]([Cl:11])[N:10]=1

Participants

5

Reactant 2

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

Product 1

HCID 15665807HCID 15665807, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Ethylene glycol (7.0 ml, 125.5 mmol) and p-toluenesulfonic acid monohydrate (0.56 g, 2.94 mmol) are added to a solution of 2,4-dichloro-thiazole-5-carboxaldehyde (7.88 g, 43.3 mmol) in toluene (100 ml). The reaction is heated at reflux and water removed via Dean-Stark for 4 h. The reaction is cooled, poured into 20% Na2CO3 (200 ml), and extracted with ethyl acetate (3×100 ml). The ethyl acetate is washed with aqueous saturated brine solution and dried over anhydrous Na2SO4. The solid is filtered off and the filtrate concentrated. The crude product is purified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes to yield (9.42 g, 96%) of 2,4-dichloro-5-([1,3]dioxolan-2-yl)-thiazole: 1H NMR (CDCl3): δ=6.07 (1H, s), 4.18-3.99 (4H, m).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux
  3. customwater removed via Dean-Stark for 4 h
  4. temperatureThe reaction is cooled
  5. additionpoured into 20% Na2CO3 (200 ml)
  6. extractionextracted with ethyl acetate (3×100 ml)
  7. washThe ethyl acetate is washed with aqueous saturated brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationThe solid is filtered off
  10. concentrationthe filtrate concentrated
  11. customThe crude product is purified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a0fb2c9f0a2141918368261623ac4131
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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