Sodium hydride → HCID 14116888, compound

HRID 1086033Notes

Reaction equation

HRID 1086033 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:10])=[C:7]([OH:22])[CH:6]=1.Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C>[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[O:10])=[C:7]([O:22][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 14116888HCID 14116888, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (420 mg of 60%, 10.5 mmoles) in DMF (10 ml) was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (1.612 g, 5 mmoles) and the mixture stirred for 20 minutes, followed by cooling (ice water) and addition of methyl bromoacetate (832 mg, 5.44 mmoles). The mixture was stirred for 20 minutes in the cold and another 10 minutes at ambient temperature followed by pouring into 70 ml of ice-cold water. A separated solid was filtered and dried to give 1.58 g of crude product mp 92°-94°. This was recrystallized from methylene chloride-ether to give 1.21 g of the title compound as a white crystalline solid, mp 94°-95° (67.6% yield). The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.2 (s, 1H); 6.16 (s, 1H); 4.7 (s, 2H); 4.40 (bs, 2H); 3.86 (s, 3H); 3.54 (m, 2H); 2.6 (m, 6H); 1.04 (t, 6H).

Workup

  1. temperatureby cooling
  2. stirringThe mixture was stirred for 20 minutes in the cold and another 10 minutes at ambient temperature
  3. filtrationA separated solid was filtered
  4. customdried
  5. customto give 1.58 g of crude product mp 92°-94°
  6. customThis was recrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-0f8cb7e3ce5b4ca9a9381c99411804b5
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

Loading…