Dimethylamine → 3-(4-Chloro-2-nitro-phenoxy)-N,N-dimethyl-benzamide

HRID 2197906Notes

Reaction equation

HRID 2197906 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][NH:22][CH3:23].O>C1COCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([N:22]([CH3:23])[CH3:21])=[O:11])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 866155003-(4-Chloro-2-nitro-phenoxy)-benzoyl chloride

Product 1

HCID 684583013-(4-Chloro-2-nitro-phenoxy)-N,N-dimethyl-benzamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product from Example 168b (2.0 g, 6.4 mmol) in THF (25 mL) was added dimethylamine (0.6 g, 13.3 mmol) and the reaction stirred for 16 h. The reaction was poured into water and extracted with ethyl acetate. The organic layer washed with 5% HCL, water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (1.9 g, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer washed with 5% HCL, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-14b8e40f0be04bcb8d31812498fa0610
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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