Diisopropylethylamine → 3-chloro-N-(3-dimethylamino-2,2-dimethyl-propyl)-4-nitro-benzamide

HRID 2234406Notes

Reaction equation

HRID 2234406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].C(N(CC)C(C)C)(C)C.[CH3:23][N:24]([CH3:31])[CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][NH2:28]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][N:24]([CH3:31])[CH3:23])=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 104477N,N,2,2-Tetramethylpropane-1,3-diamineHCID 1907761455737-29-62×

Product 1

HCID 686816653-chloro-N-(3-dimethylamino-2,2-dimethyl-propyl)-4-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-chloro-4-nitro-benzoyl chloride (Intermediate 54; 2.2 g, 10.00 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (2.095 mL, 12.00 mmol) added. The mixture was cooled in an ice/water bath and N,N,2,2-tetramethyl-1,3-propanediamine (3.652 mL, 10.00 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 h. The mixture was washed with brine, 2N NaOH (aq.), dried (MgSO4) and concentrated. Column chromatography of the residue (2% MeOH/DCM) gave the title compound as a yellow oil 17171/2/1 (2.29 g, 77%).

Workup

  1. temperatureThe mixture was cooled in an ice/water bath
  2. washThe mixture was washed with brine, 2N NaOH (aq.)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b720f0db77746e78d781feafdbd90c6
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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