Hydrochloric Acid → HCID 19754865, compound

HRID 1588926Notes

Reaction equation

HRID 1588926 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].[CH2:14]([N:20]([CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>N1C(C)=CC(C)=CC=1C>[CH:30]1([N:20]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([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)=[CH:24][CH:23]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 695053,4,5-TrimethoxyphenolHCID 54086681HCID 54086681, compound

Product 1

HCID 19754865HCID 19754865, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A slurry of cuprous oxide (300 mg, 2.1 mmol) in a solution of 3,4,5-trimethoxyphenol (736 mg, 4.0 mmol) and p-bromobenzoic acid N-n-hexyl-N-cyclohexyl amide (1.47 g, 4.0 mmol) in 2,4,6-collidine (20 ml) is refluxed with stirring under a nitrogen atmosphere for 18 hr. The reaction is cooled, poured onto dilute aqueous HCl and extracted three times with ethyl acetate. The combined organic layers are washed twice with saturated aqueous NaCl solution, twice with 5% NaOH solution, twice with saturated NaCl solution and dried (Na2SO4). The drying agent is filtered and the filtrate concentrated in vacuo to give the crude product. This material is chromatographed on silica gel using mixtures of ethyl acetate and hexane as the eluents to give the title compound.

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed twice with saturated aqueous NaCl solution, twice with 5% NaOH solution, twice with saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. filtrationThe drying agent is filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give the crude product
  8. customThis material is chromatographed on silica gel using mixtures of ethyl acetate and hexane as the eluents

Sources & evidence

ORD record
ord-e75cd8ea39404f1e9e3a6db3d4921cee
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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