Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1177130Notes

Reaction equation

HRID 1177130 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([CH3:14])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

Product 1

HCID 1403894-bromo-N,N-dimethylbenzamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (2.00 g, 9.11 mmol) and dimethyl amine hydrochloride (892 mg, 10.90 mmol) in 20 mL of CH2Cl2 was added triethylamine (3.81 mL, 27.30 mmol). The mixture was stirred at room temperature for 2 h, quenched with water, extracted with 3×CHCl3, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2 to give a white solid (1.73 g, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.48-7.65 (m, 2 H) 7.20-7.37 (m, 2 H) 3.05 (d, J=50.78 Hz, 6 H); LCMS for C9H10BrNO m/z 228.00 and 230.00 (M+H)+

Workup

  1. customquenched with water
  2. extractionextracted with 3×CHCl3
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-dbe5a481fed240deb2d26db14fe096b8
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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