Oxalyl chloride → 4-bromo-N-(4-chlorophenethyl)-3-methylbenzamide

HRID 510772Notes

Reaction equation

HRID 510772 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].C(Cl)(=O)C(Cl)=O.C(N(C(C)C)C(C)C)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1>ClCCl.CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:36][CH2:35][CH2:34][C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)=[O:8])=[CH:4][C:3]=1[CH3:11]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 670809004-bromo-N-(4-chlorophenethyl)-3-methylbenzamideYield 48.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-bromo-3-methylbenzoic acid (0.500 g, 2.325 mmol) in dichloromethane (10 ml) and DMF (1 drop) was added oxalyl dichloride (0.2231 ml, 2.558 mmol), and the reaction was stirred for 30 minutes. N-ethyl-N-isopropylpropan-2-amine (0.8934 ml, 5.115 mmol) and 2-(4-chlorophenyl)ethanamine (0.3557 ml, 2.558 mmol) were added, and the reaction was stirred for 1 hour at ambient temperature. The reaction was diluted with EtOAc and washed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by recrystallization from EtOAc and hexanes to yield 400 mg of the title compound (48.78% yield).

Workup

  1. stirringthe reaction was stirred for 1 hour at ambient temperature
  2. washwashed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by recrystallization from EtOAc and hexanes

Sources & evidence

ORD record
ord-612c6cd0a39447dcb20e177cfd7a8789
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

Loading…