Ethylene Glycol → HCID 58336728, compound

HRID 2358984Notes

Reaction equation

HRID 2358984 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:32](O)[CH2:33][OH:34]>>[CH3:19][C:18]1([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:10]3[CH:9]=[N:8][N:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:11]=3)[N:17]=2)[O:34][CH2:33][CH2:32][O:20]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 58336803HCID 58336803, compound

Product 1

HCID 58336728HCID 58336728, compound

Procedure

In 100 ml of 1,1,1-benzotrifluoride, 0.13 g (0.49 mmol) of 1-[6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridin-2-yl]ethanone, 0.1 g (0.58 mmol) of 4-toluenesulphonic acid and 1.8 ml (32 mmol) of 1,2-ethanediol were heated under reflux in a reflux apparatus with Soxleth extractor which had been charged with 4 Å molecular sieve for 2 h. The reaction mixture concentrated by evaporation, ethyl acetate, dil. aqueous sodium hydroxide solution, citrate buffer to pH=9 and also aq. NaCl were added to the residue, the aqueous phase was extracted twice with ethyl acetate, the combined organic phases were dried with MgSO4 and concentrated by evaporation. The residue was purified by chromatography on silica gel (petroleum ether/acetone).

Workup

  1. temperatureunder reflux in a reflux apparatus with Soxleth extractor which
  2. additionhad been charged with 4 Å molecular sieve for 2 h
  3. concentrationThe reaction mixture concentrated by evaporation, ethyl acetate, dil. aqueous sodium hydroxide solution, citrate buffer to pH=9 and also aq. NaCl
  4. additionwere added to the residue
  5. extractionthe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialthe combined organic phases were dried with MgSO4
  7. concentrationconcentrated by evaporation
  8. customThe residue was purified by chromatography on silica gel (petroleum ether/acetone)

Sources & evidence

ORD record
ord-e7ba13fec275458cb4ffe3fbf8c3d42a
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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