2,6-Dimethoxybenzoyl chloride → HCID 18368343, compound

HRID 379695Notes

Reaction equation

HRID 379695 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23](Cl)=[O:24]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:23](=[O:24])[C:22]2[C:26]([O:30][CH3:31])=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH3:19])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 18173954tert-Butyl [2-(4-aminophenoxy)ethyl]carbamate

Product 1

HCID 18368343HCID 18368343, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder.

Workup

  1. additionwas added into the solution
  2. concentrationthe reaction mixture was concentrated under vacuum and residue
  3. dissolutionwas dissolved into chloroform (30 ml)
  4. washThe solution was washed with 1N sodium hydroxide aqueous solution (30 ml)
  5. distillationSolvent was distilled out
  6. customresidue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-ad248fe92edc4be1b7de9b2b93d61357
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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