4-Nitrobenzoic Acid → N,N-Dimethyl-4-nitro-benzamide

HRID 2092512Notes

Reaction equation

HRID 2092512 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][N:14](C=O)[CH3:15].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>O>[CH3:13][N:14]([CH3:15])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 138975N,N-Dimethyl-4-nitro-benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-nitro-benzoic acid (20 g, 0.1196 mol) in DMF (300 mL) N,N-dimethylamine hydrochloride (11.7 g, 0.1436 mol), HOBt (20.9 g, 0.1554 mol), EDC.HCl (34.3 g, 0.1794 mol) and DIPEA (30.91 g, 0.2392 mol) were added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×500 mL). The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound [23.0 g, 99%]; LC-MS (ESI): Calculated mass: 194.1; Observed mass: 195.1 [M+H]+ (RT: 1.70 min).

Workup

  1. extractionextracted with ethyl acetate (3×500 mL)
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6ca83c2f89bb4a5b9aeaa0500270bbdd
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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