Ethylene Glycol → HCID 59435991, compound

HRID 1802489Notes

Reaction equation

HRID 1802489 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[Cl:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH2:30](O)[CH2:31][OH:32]>C1C=CC=CC=1>[Cl:12][C:3]1[CH:4]=[C:5]([C:9]2([CH3:10])[O:32][CH2:31][CH2:30][O:11]2)[CH:6]=[C:7]([Cl:8])[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6048121-(4-Amino-3,5-dichlorophenyl)ethan-1-oneHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 59435991HCID 59435991, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-(4-Amino-3,5-dichlorophenyl)ethanone (15 g, 73.5 mmol), pyridinium p-toluene sulfonic acid (5.5 g, 22 mmol), and ethylene glycol (6.2 mL, 110 mmol) were heated together in benzene (250 mL) with a Dean Stark trap at 100° C. overnight. The benzene was distilled off until ˜75 mL remained and the reaction mixture was extracted with EtOAc and saturated NaHCO3. The organic layer was separated, dried with MgSO4, filtered, and concentrated under rotary evaporation to afford a oily residue. The crude mixture was purified on silica gel chromatography (100% Hex to 100% EtOAc) to afford the desired product.

Workup

  1. distillationThe benzene was distilled off until ˜75 mL
  2. extractionthe reaction mixture was extracted with EtOAc and saturated NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under rotary evaporation
  7. customto afford a oily residue
  8. customThe crude mixture was purified on silica gel chromatography (100% Hex to 100% EtOAc)

Sources & evidence

ORD record
ord-c178203498d5466681c752928b186431
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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