Hydrochloric Acid → HCID 19754878, compound

HRID 1588931Notes

Reaction equation

HRID 1588931 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([OH:16])[CH:7]=[C:8]([O:13][CH2:14][CH3:15])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[CH:17]([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)([CH3:19])[CH3:18].Cl>N1C(C)=CC(C)=CC=1C>[CH:30]1([N:20]([CH:17]([CH3:19])[CH3:18])[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([O:16][C:6]3[CH:7]=[C:8]([O:13][CH2:14][CH3:15])[C:9]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)=[CH:24][CH:23]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19754886HCID 19754886, compoundHCID 19754898HCID 19754898, compound

Product 1

HCID 19754878HCID 19754878, 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-triethoxyphenol (777 mg, 4.0 mmol) and p-bromobenzoic acid N-isopropyl-N-cyclohexyl amide (1.30 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-70e81df18bbb4d0dbf65b2187b159ae6
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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