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

HRID 1258632Notes

Reaction equation

HRID 1258632 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]>C1COCC1>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochloride

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) were added to 4-chloro-3-nitrobenzylamine hydrochloride (5.00 g, 22.4 mmol) in THF (100 mL). The reaction mixture was diluted with THF and stirred at rt for 1.5 h. The mixture was filtered and washed. The filtrate was concentrated to give the sub-title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-41ea255f469542e2a9c992d739622770
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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