Ethylene Glycol → HCID 178520159, compound

HRID 1067707Notes

Reaction equation

HRID 1067707 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH:18]3[CH2:20][CH2:19]3)=O)=[CH:12][CH:11]=2)[N:3]=[CH:2]1.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1.[CH2:32]([OH:35])[CH2:33][OH:34]>>[CH2:32]1[O:35][C:18]([CH2:20][CH2:19][OH:28])([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][C:4]3[N:3]=[CH:2][NH:1][CH:5]=3)=[CH:15][CH:14]=2)[O:34][CH2:33]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 178519714HCID 178519714, compound

Product 1

HCID 178520159HCID 178520159, compound

Procedure

1.3 mmol of cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl ketone (Example 61) and a catalytic amount of 4-toluenesulphonic acid in 15 ml of ethylene glycol are brought to reflux for 5 hours. The solvent is evaporated off under reduced pressure, and the residue is dissolved in 10 ml of H2O and alkalized with ammonia. The crude product is extracted with dichloromethane and purified by rotatory chromatography (eluent: dichloromethane/methanol (99:1-90:10), ammoniacal atmosphere). The product is crystallized in the form of hydrogen maleate from diethyl ether and ethanol.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe solvent is evaporated off under reduced pressure
  3. dissolutionthe residue is dissolved in 10 ml of H2O
  4. extractionThe crude product is extracted with dichloromethane
  5. custompurified by rotatory chromatography (eluent: dichloromethane/methanol (99:1-90:10), ammoniacal atmosphere)
  6. customThe product is crystallized in the form of hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-103e0edb335b4578a355c04e66ce9845
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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