Hydrochloric Acid → HCID 9845428, compound

HRID 1588896Notes

Reaction equation

HRID 1588896 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].Br[C:15]1[CH:32]=[CH:31][C:18]([C:19]([N:21]([CH:28]([CH3:30])[CH3:29])[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:20])=[CH:17][CH:16]=1.Cl>N1C(C)=CC(C)=CC=1C>[CH:22]1([N:21]([CH:28]([CH3:30])[CH3:29])[C:19](=[O:20])[C:18]2[CH:31]=[CH:32][C:15]([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:16][CH:17]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 695053,4,5-TrimethoxyphenolHCID 19754886HCID 19754886, compound

Product 1

HCID 9845428HCID 9845428, 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 4-bromo-N-isopropyl-N-cyclohexyl benzamide (1.290 g, 3.98 mmol) in 2,4,6-collidine (20 ml) was refluxed with stirring under a nitrogen atmosphere for 18 hr. The reaction was cooled, poured onto dilute aqueous HCl and extracted three times with ethyl acetate. The combined organic layers were washed twice with saturated aqueous NaCl solution, 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 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, melting point 124.01° C. (DSC).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were 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 was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give 1.29 g of crude product
  8. customThis material was chromatographed on silica gel using mixtures of ethyl acetate and hexane as the eluents

Sources & evidence

ORD record
ord-abd43339124c41b083c3ee4e2b2694ac
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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