Water → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-propoxy)-benzamide

HRID 1382948Notes

Reaction equation

HRID 1382948 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.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29](=[O:31])[CH3:30].O>CN(C=O)C>[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][CH2:28][C:29](=[O:31])[CH3:30])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 141168894-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-propoxy)-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (5.0 g, 16 mmoles) and potassium carbonate (10.62 g, 77 mmoles) in DMF (25 ml) was added chloroacetone (2.32 g of 90%, 22 mmoles) and the mixture stirred vigorously for 5 hours, followed by pouring into water (130 ml) and filtration to give, after drying, 4.57 g of crude product. This was dissolved in methylene chloride and filtered over a short alumina column, followed by concentration and recrystallization of the residue from toluene to give 4.16 g (78%) of the title compound as white solid, mp 105°-106.5°. The NMR (90 MHz) in CDCl3 gave the following resonances: ε 8.44 (s, 1H); 8.24 (s, 1H); 6.16 (s, 1H); 4.72 (s, 2H); 4.4 (s, 2H); 3.6 (m, 2H); 2.68 (m, 6 H); 2.28 (s, 3H); 1.08 (t, 6H).

Workup

  1. customto give
  2. customafter drying
  3. dissolutionThis was dissolved in methylene chloride
  4. filtrationfiltered over a short alumina column
  5. concentrationfollowed by concentration and recrystallization of the residue from toluene

Sources & evidence

ORD record
ord-2ea2b72758fa48e18141c5c640cadf68
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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