Hydrochloric Acid → HCID 19754881, compound

HRID 1588913Notes

Reaction equation

HRID 1588913 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH:14]([N:17]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22](Br)=[C:21]([O:26][CH3:27])[CH:20]=1)([CH3:16])[CH3:15].Cl>N1C(C)=CC(C)=CC=1C>[CH:29]1([N:17]([CH:14]([CH3:16])[CH3:15])[C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([O:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:21]([O:26][CH3:27])[CH:20]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 695053,4,5-Trimethoxyphenol2×HCID 54197126HCID 54197126, compound

Product 1

HCID 19754881HCID 19754881, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A slurry of cuprous oxide (1.00 g, 6.78 mmol) in a solution of 3,4,5-trimethoxyphenol (1.62 g, 8.53 mmol) and 4-bromo-3-methoxybenzoic acid N-isopropyl-N-cyclohexyl amide (2.42 g, 6.8I mmol) in 2,4,6-collidine (30 ml) was refluxed with stirring under a nitrogen atmosphere for 36 hr. Additional 3,4,5-trimethoxyphenol (0.32 g), and cuprous oxide (0.16 g) were added and reflux continued for 72 hrs. The reaction mixture was cooled, poured onto 6N HCl and extracted three times with ethyl acetate. The combined organic layers were washed twice with 5% NaOH solution, twice with saturated NaCl solution and dried (Na2SO4) The drying agent was filtered and the filtrate concentrated in vacuo to give 1.29 g of crude product. This material was chromatographed twice on silica gel using mixtures of ethyl acetate and hexane as the eluents to give the title compound as a crystalline solid that could be recrystallized from ethyl acetate hexane, m. pt. 126-128° C.

Workup

  1. temperaturereflux
  2. waitcontinued for 72 hrs
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed twice with 5% NaOH solution, twice with saturated NaCl solution
  6. dry with materialdried (Na2SO4) The drying agent
  7. filtrationwas filtered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto give 1.29 g of crude product
  10. customThis material was chromatographed twice on silica gel using mixtures of ethyl acetate and hexane as the eluents

Sources & evidence

ORD record
ord-c6c52f9e5c604cb8a3ce50a78ef3b9eb
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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