Water → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methyl-2-oxo-butoxy)-benzamide

HRID 620268Notes

Reaction equation

HRID 620268 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+].O.Br[CH2:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32]>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][CH2:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 108990371-Bromo-3-methylbutan-2-oneHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 141168954-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methyl-2-oxo-butoxy)-benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (5.82 g, 18 mmoles), anhydrous potassium carbonate (12.48 g; 90 mmoles) in DMF (30 ml) and 1-bromo-3-methyl-2-butanone [4.5 g, 27 mmoles; prepared according to M. Gaudry and A. Marquet, Org. Syn. 55, 24 (1976)] was stirred for 20 hours under nitrogen. The mixture was poured into water (150 ml) and the solid collected, dried and crystallized from toluene to give the title compound (4.86 g, 73%), mp. 109°-110°. The NMR spectrum (90 MHz) gave the following resonances: δ 8.56 (bt, 1H); 8.24 (s, 1H); 6.18 (s, 1H); 4.8 (s, 2H); 4.44 (s, 2H) 3.56 (m, 2H); 2.62 (m, 7H); 1.2 (d, 6H); 1.06 (t, 6H).

Workup

  1. customprepared
  2. customthe solid collected
  3. customdried
  4. customcrystallized from toluene

Sources & evidence

ORD record
ord-3c9197ac8de24e9ab5c73520f7e827e0
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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