2-Bromobenzoic acid → 2-bromo-N,N-diethylbenzamide

HRID 1592707Notes

Reaction equation

HRID 1592707 reaction equation
C1C=CC2N(O)N=NC=2C=1.[CH3:11][CH2:12][N:13](C(C)C)[CH:14](C)[CH3:15].[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.C(NCC)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:13]([CH2:14][CH3:15])[CH2:12][CH3:11])=[O:25]

Participants

7

Reactant 5

HCID 69402-Bromobenzoic acidHCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 6690442-bromo-N,N-diethylbenzamideYield 129.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBT (2.72 g, 10.08 mmol), DIPEA (3.52 mL, 20.16 mmol), 2-bromo benzoic acid (4.08 g, 10.08 mmol), and diethyl amine (2.08 mL, 10.08 mmol) were dissolved in DCM (100 mL) and stirred at r.t. for about 30 minutes. EDCI (3.86 g, 10.08 mmol) was added, and the mixture was stirred at r.t. for about 16 hours. The reaction was concentrated to an oil, and the oil was purified via column chromatography to give 2-bromo-N,N-diethyl-benzamide (3.35 g, 68%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at r.t. for about 16 hours
  2. concentrationThe reaction was concentrated to an oil
  3. customthe oil was purified via column chromatography

Sources & evidence

ORD record
ord-a173b33f57344b8ba2c9460bd4ba0d1a
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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