Pyridine → 4-[(8-Bromooctanoyl)amino]benzamide

HRID 1675682Notes

Reaction equation

HRID 1675682 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26]>C(#N)CCC>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1)=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 760794-AminobenzamideHCID 114022288-bromooctanoyl Chloride

Product 1

HCID 580247434-[(8-Bromooctanoyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent2×

Conditions

Temperature
20 °C

Procedure

Pyridine (1.6 mL, 1.1 equivalents) is added to a mixture of 4-aminobenzamide (2.5 g, 18 mmol) and n-butyronitrile (65 mL) at 20° C. under an atmosphere of nitrogen. The mixture is stirred for 15 minutes before a solution of 8-bromooctanoyl chloride (3.7M in toluene, 5.5 mL, 20 mmol, 1.1 equivalents) in n-butyronitrile (10 mL) is added over 20 minutes. The mixture is then stirred at 20° C. for 22 hours. Upon complete reaction the mixture is filtered. The resulting product is washed with methanol (10 mL), water (2×25 mL), methanol (10 mL) and tert-butyl methyl ether (TBME, 10 mL) before being dried in vacuo to yield the title compound, generally as a solid.

Workup

  1. additionis added over 20 minutes
  2. customUpon complete reaction the mixture
  3. filtrationis filtered
  4. washThe resulting product is washed with methanol (10 mL), water (2×25 mL), methanol (10 mL) and tert-butyl methyl ether (TBME, 10 mL)
  5. custombefore being dried in vacuo

Sources & evidence

ORD record
ord-dcfd7b23d8e041249a2b296729377658
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

Loading…