2-Chloroacetophenone → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-2-phenyl-ethoxy)-benzamide

HRID 1382949Notes

Reaction equation

HRID 1382949 reaction equation
[Na].Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([OH:21])[CH:5]=1.Cl[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25]>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])=[O:9])=[C:6]([O:21][CH2:23][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:5]=1

Participants

4

Reactant 3

HCID 107572-ChloroacetophenoneHCID 5360545SodiumHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 141168904-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-2-phenyl-ethoxy)-benzamideYield 50.1%

Procedure

To a stirred suspension of sodium hdride (320 mg of 60%, 8 mmoles, washed with n-pentane) in DMF (15 ml) was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (1.289 g, 4 mmoles) and the mixture stirred for 20 minutes followed by addition of chloroacetophenone (619 mg, 4 mmoles). The mixture was stirred 4 hours, poured into ice-cold water (50 ml) whereupon a solid separated out. This was isolated by filtration, dried and recrystallized from methanol to give 810 mg (50%) of the title compound as white solid mp 153°-4°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ8.64 (bs, 1H); 8.2 (s, 1H); 8 (m, 2H); 7.6 (m, 3H); 6.22 (s, 1H); 5.36 (s, 2H); 4.4 (s, 2H); 3.52 (m, 2H); 2.64 (m, 6H); 1.01 (m, 6H).

Workup

  1. washhdride (320 mg of 60%, 8 mmoles, washed with n-pentane) in DMF (15 ml)
  2. stirringThe mixture was stirred 4 hours
  3. customseparated out
  4. customThis was isolated by filtration
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d3e123357c084a31bda7bf0990022bb9
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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