Diethylamine → 2-Chloro-N,N-diethyl-4-nitrobenzeneacetamide

HRID 1820862Notes

Reaction equation

HRID 1820862 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:16][C:17](Cl)=[O:18]>C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:16][C:17]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:18]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 85969188(2-Chloro-4-nitrophenyl)acetic acid chloride

Product 1

HCID 688195332-Chloro-N,N-diethyl-4-nitrobenzeneacetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

5.67 mL (54.0 mmol) of diethylamine is dissolved in 50 mL of ethyl acetate and 3.20 g (13.7 mmol) of (2-chloro-4-nitrophenyl)acetic acid chloride (VI.1.a) in 50 mL of ethyl acetate is slowly added dropwise at 0° C. Then the mixture is stirred for another 2 hours at ambient temperature. After this time, some more ethyl acetate is added and the mixture is washed twice with water and twice with saturated saline solution. The organic phase is dried over sodium sulfate, the solvent is eliminated and the residue is dried in vacuo. Yield: 3.70 g (100% of theory); Rf value: 0.45 (silica gel, petroleum ether/ethyl acetate=1:1); C12H15ClN2O3; EII mass spectrum: m/z=271/273 [M+H]+.

Workup

  1. washthe mixture is washed twice with water and twice with saturated saline solution
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-cf6c75d5631741feb3083f64c3dddc10
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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