2,6-Dimethoxybenzoyl chloride → HCID 9909405, compound

HRID 379700Notes

Reaction equation

HRID 379700 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:20](=[O:21])[C:19]2[C:23]([O:27][CH3:28])=[CH:24][CH:25]=[CH:26][C:18]=2[O:17][CH3:16])=[CH:11][CH:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 4189324-(2-(Diethylamino)ethoxy)aniline

Product 1

HCID 9909405HCID 9909405, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N,N-diethyl-2-(4-aminophenoxy)ethylamine (4.00 g) was added into 2,6-dimethoxybenzoic acid chloride (4.20 g) in pyridine (40 ml) in an ice bath. After stirred for one hour at room temperature, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (50 ml). The solution was washed with 1N sodium hydroxide aqueous solution followed by water and then saturated sodium chloride (50 ml, each). Solvent was distilled out and residue was purified by silica-gel column chromatography (chloroform:methanol=25:1) to obtain 4′-[2-(diethylamino)ethoxy]-2,6-dimethoxybenzanilide (5.01 g) as color-less crystal.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum and residue
  2. dissolutionwas dissolved into chloroform (50 ml)
  3. washThe solution was washed with 1N sodium hydroxide aqueous solution
  4. distillationSolvent was distilled out
  5. customresidue was purified by silica-gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-3734e17dd52542dd932d04f55a013a9c
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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