Pivaloyl chloride → N-(4-Chloro-3-nitrobenzyl)-2,2-dimethyl-propionamide

HRID 2042811Notes

Reaction equation

HRID 2042811 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]>C1COCC1>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:14][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 18796740(4-Chloro-3-nitrophenyl)methanamine

Product 1

HCID 66765017N-(4-Chloro-3-nitrobenzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

TEA (8.00 mL, 57.5 mmol) followed by pivaloyl chloride (2.80 mL, 22.8 mmol) in THF (25 mL) are added to 4-chloro-3-nitrobenzylamine (5.00 g) in THF (100 mL). The reaction mixture is diluted with THF and stirred at rt for 1.5 h. The mixture is filtered and washed and the filtrate is concentrated.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-82f6152cfeb04c0cbbad98eea7d5d7ae
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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