Butylamine → N-butyl-2,3-dimethoxybenzamide

HRID 1725240Notes

Reaction equation

HRID 1725240 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:14]([NH:18][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:3]=1[O:2][CH3:1])[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 152042,3-Dimethoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 347459N-butyl-2,3-dimethoxybenzamideYield 94.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dimethoxybenzoic acid (4.55 g, 25.0 mmol) in metylene chloride (250 mL) were added butylamine (2.01 g, 27.5 mmol) and DMAP (3.36 g, 27.5 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g, 27.5 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was washed with 5% HCl (3×100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL) and dried over MgSO4. Concentration in vacuo afforded 5.59 g (94%) of a colourless oil.

Workup

  1. washThe resulting solution was washed with 5% HCl (3×100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-e049793ba1ab42e0a98e1d470f0ffdd8
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

Loading…