1,2-Dichloroethane → HCID 66699138, compound

HRID 1095933Notes

Reaction equation

HRID 1095933 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[N:6]1.[Cl:13]CCCl>S(Cl)(Cl)=O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][Cl:13])[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 66699126HCID 66699126, compound

Product 1

HCID 66699138HCID 66699138, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

(4-Hydroxymethyl-pyrazol-1-yl)-acetic acid methyl ester (194 mg) was dissolved in 1,2-dichloroethane (2 mL) and thionylchloride (0.7 mL). The solution was refluxed for 2.5 hours. The reaction was cooled and concentrated in vacuo. The residue was poured into ice/water and basified with sat. Na2CO3 to pH 11. The aqueous phase was then extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=100:0 to 50:50) to give the title compound as a colorless oil (81 mg, 36%). MS (EI)=188.0 [M+].

Workup

  1. temperatureThe solution was refluxed for 2.5 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. additionThe residue was poured into ice/water and basified with sat. Na2CO3 to pH 11
  5. extractionThe aqueous phase was then extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-df027104f9e347108f2772a3753ef06b
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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