3,4,5-Trimethoxyphenol → HCID 19754863, compound

HRID 1588908Notes

Reaction equation

HRID 1588908 reaction equation
[CH:1]1([N:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:7](=[O:16])[C:8]2[CH:13]=[CH:12][C:11](Br)=[C:10]([CH3:15])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([OH:35])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32]>N1C(C)=CC(C)=CC=1C>[CH:17]1([N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7](=[O:16])[C:8]2[CH:13]=[CH:12][C:11]([O:35][C:27]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=3)=[C:10]([CH3:15])[CH:9]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 695053,4,5-TrimethoxyphenolHCID 19754882HCID 19754882, compound

Product 1

HCID 19754863HCID 19754863, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

The reaction and workup were carried out in the same manner as described in Example 1 using 4-bromo-3-methyl benzoic acid N-cyclopentyl-N-cyclohexyl amide (983 mg, 2.7 mmol), 3,4,5-trimethoxy phenol (983 mg, 2.7 mmol) and cuprous oxide (200 mg, 1.3 mmol) in 2,4,6-collidine (15 ml). The crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound as a crystalline solid that could be recrystallized from ethyl acetate and hexane, m. pt. 181-182° C.

Workup

  1. customThe reaction and workup
  2. customThe crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-bb7ca9a1be9246dda83d416b34685592
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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