Ethylene Glycol → HCID 15665807, compound

HRID 577063Notes

Reaction equation

HRID 577063 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>C(=O)([O-])[O-].[Na+].[Na+].O.CC1C=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

6

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehyde

Product 1

HCID 15665807HCID 15665807, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 10340Sodium CarbonateSolvent

Procedure

In a round bottom flask equipped with a Dean-Stark trap was charged ethylene glycol (2.3 mL, 41.1 mmol), 2,4-dichloro-1,3-thiazole-5-carbaldehyde (2.5 g, 13.7 mmol), and toluene (35 mL). To this solution was added 4-methylbenzene-1-sulfonic acid hydrate (210 mg, 1.1 mmol). The reaction mixture was stirred at reflux overnight. After cooling to room temperature, the solution was poured in 10% sodium carbonate solution (50 mL). The mixture was extracted with EtOAc (2×35 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 2,4-dichloro-5-(1,3-dioxolan-2-yl)-1,3-thiazole (2.9 g, 93% yield). The product was used without further purification.

Workup

  1. customIn a round bottom flask equipped with a Dean-Stark trap
  2. temperatureat reflux overnight
  3. extractionThe mixture was extracted with EtOAc (2×35 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-cadca88d12e04979bf6d3d8ec96005cd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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