Benzoyl chloride, 3-nitro- → HCID 883681, compound

HRID 1514810Notes

Reaction equation

HRID 1514810 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14])([O-:9])=[O:8]>C1COCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 883681HCID 883681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylethylendiamine (14.25 g, 61.0 mmol) was added dropwise into a solution of commercially available 3-nitrobenzoyl chloride (25.0 g, 134 mmol) in dry THF (150 mL) at 0° C. and stirred for 45 min. The reaction mixture was evaporated to under reduce pressure to dryness and residue was recrystallized from EtOH to give N-(2-dimethylaminoethyl)-3-nitrobenzamide; 31.0 g (97%); mp 89-90° C.; 1H NMR (CDCl3) δ 2.29 (6H, s, 2×Me), 2.57 (2H, t, J=5.8 Hz, CH2), 3.57 (2H, q, J=5.6 and 5.8 Hz, CH2), 7.37 (1H, brs, exchangeable, NH), 7.63 (H, d, J=7.9 Hz, ArH) 8.19 (1H, m, ArH), 8.33 (1H, m, ArH), 8.66 (1H, s, ArH). Anal. Calcd. for (C13H21N3O3): C, 58.41, H, 7.92, N, 15.72. Found: C, 58.23, H, 7.69, N, 15.90.

Workup

  1. customThe reaction mixture was evaporated
  2. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-da7b309f982644e6b99874e635363130
Source dataset
uspto-grants-2012_07
Patent number
US08222297B2

Reaction notes

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