Potassium Carbonate → 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-methoxyethoxy)benzamide

HRID 620247Notes

Reaction equation

HRID 620247 reaction equation
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])=[C:5]([OH:20])[CH:4]=1.ClC[CH2:23][CH2:24][O:25][CH2:26]CCCl.C(=O)([O-])[O-].[K+].[K+].[Br-].[Na+]>CN(C)C=O>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])=[C:5]([O:20][CH2:23][CH2:24][O:25][CH3:26])[CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12383Propane, 1,1'-oxybis(3-chloro-HCID 253881Sodium BromideHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 141169374-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-methoxyethoxy)benzamideYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixature of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (2.50 g, 7.76 mmoles), 2-chloro-ethylmethylether (1.47 g, 15.5 mmoles), potassium carbonate (2.14 g, 15.5 mmoles) and sodium bromide (0.80 g, 7.76 mmoles) in 40 ml of dimethylformamide (DMF) was stirred at reflux for four hours. The DMF was removed under vacuum and the residue was redissolved in methylene chloride and washed with water and dilute NaOH. The solvent was evaporated and the product was chromatographed using a gradient elution of methanol-methylene chloride containing 0.25% NH4OH. The appropriate fractions were combined and evaporated to yield 2.34 g (87.6%) of cream-colored solid. Recrystallization of the residue from ethyl acetate gave the title compound as a white solid, mp 108°-110.5°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.19 (s, 1H); 6.35 (s, 1H); 4.5 (bs, 2H); 4.2 (m, 2H); 3.8 (m, 2H); 3.5 (m, 2H); 3.49 (s, 3H); 2.59 (m, 6H); 1.02 (t, 6H).

Workup

  1. temperatureat reflux for four hours
  2. customThe DMF was removed under vacuum
  3. dissolutionthe residue was redissolved in methylene chloride
  4. washwashed with water and dilute NaOH
  5. customThe solvent was evaporated
  6. customthe product was chromatographed
  7. washa gradient elution of methanol-methylene chloride containing 0.25% NH4OH
  8. customevaporated

Sources & evidence

ORD record
ord-1a537b1273a54bfda6d458ee9ec3497e
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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